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21

III

21 1. 2. I

3. 4. 123 45 612 78 9 10 1113 1416 15 2001 5 II

...(1)...(1)...(6)...(14)...(15)...(19)...(19)...(26)...(40)...(42)...(46)...(46)...(55)...(71)...(75)...(81)...(81)...(84)...(99)...(103)...(109)...(109)...(114)...(131)...(134)...(141)...(141)...(144)...(150)...(154)...(159)...(159)...(162)...(188) 1

...(191)...(199)...(199)...(203)...(233)...(236)...(242)...(242)...(251)...(276)...(282)...(294)...(294)...(299)...(308)...(309)...(313)...(313)...(315)...(335)...(339)...(348)...(348)...(353)...(360)...(368)...(372)...(372)...(380)...(397)...(400)...(415)...(415)...(418)...(424)...(429)...(433) 2

...(433)...(443)...(454)...(456)...(460) () ()...(460) () ()...(466) () ()...(471) () ()...(476) () ()...(482) () ()...(489) ()...(496) ()...(507) ()...(515) ()...(522) ()...(531) ()...(542) ()...(550) ()...(561) ()...(571)...(580) 3

1. (1) a. b. c. d. (2) a. b. c. (3) a. [m.n]b. c. 6 7 3 5 4 1 2 4--[2.4] (4) a. b. c. 7 1 2 8 2, 3, 8-[3.2.1] 6 5 3 4 2. (1) n 2n2 s p sp 3 s sp 3 σ 109 28 (2) σ Newmann() 1

(3) sp 3 2 (4) 109 28 99.9% (5) a e a 109 28 e e (6) 3. (1) R X 2 RX (X, ) 2 2 400~600 R' R'' (R', R''<R) 2 2 n 2n2 1 ~ 4 2 (2) Al 3 2 2 300 ( ) 3 2 () () 2 XX 2 a. Ni 2 80 2 Ni 2 200 2 2 2

b. 2 4 2 2 2 2 2 2 4. ()() X 2X 2 R X R X R X RX X 2 R X RX R R R R X X X 2 >>> 5. (1) 2 /Ni R' R" R' 2 2 R" R' ()R" (Grignard) (2) Wrtz Zn/g N 2 N 2 R' 2 R"() R X LiAl 4 Zn, R R MgX 2 R Na(a) RNa R Na 2 3 R X Na R R 3

oreyouse 2 R MgX R Li ux R'X R R' R MgX AgI R R RX Kolbe RNa 2 R R Na 2 3 2 (3) 2 2 2 Na Zn 2 2 R' R" 3 Na 2 R' R" Zn/ R' R" 2 2 (Diels-Alder) 2 2 2 2 2 2 2 2 2 /Ni [ 1] (1) 2 2 2 2 2 2 (2) 2 2 2 2 (3) 2 2 2 (4) 2 2 2 2 4

(5) (6) (1) 5, 5--4- (2) 2, 6--4- (3) 2, 5, 5--3- (4) 2, 2, 5--4- (5) 3, 6--8- (6) 3--3- [ 2] ( ) 2 (1) (2) (3) (4) (5) (6) (1) -1--3- (2) -1--3- (3) 5-[2.5] (4) 3-[3.3.0] (5) 5-[3.4] (6) 2-[2.2.1] [ 3] (1) 2 2 I (2) (a) ( 2 ) 4 (b) ( 2 ) 2 2 2 2 (c) 2 (d) 2 2 2 3 (1) < 2 < 2 I (2) (c)<(b)<(a)<(d) [4] 2 2 5

(a) (b) (a)(a) [ 5] (1) (2) -1--3- (3) -1--2- (4) -1--2- (1) (2) ( ) 2 ( ) 2 1 (3) ( ) 2 (4) ( ) 2 2 (1) e (2) e (3) ( ( ) 2 ) e ( ) a (4) e [ 6] 7 14 7 14 4 2 2 2 2 2 2 [ 7] σ 6

2 2 33 2 5 2 5 [8] hν R S 2 2 R S 2 (1) hν S 2 2 S 2 S 2 S 2 (2) R R R S 2 2 R S 2 (3) R R R R R R 2 [ 9] 2-3 () 2 2 2 2 3 5 3 >2 >1 >, 2 [10] 2- ( ) 2 2 2 300 2 ( ) 2 ( ) 2 2 34% 22% ( ) 2 ( ) 2 2 2 28% 16% 3 >2 >1 > 7

2-9 (1 )2 (2 )1 (3 ) V (1 ) V (2 ) 34 % 16% 28% 22% (3 ) = = 12.523.96 9 2 1 >> 3 >2 >1 > [11] 2 ( ) 3 ( ) 2 2 ( ) 3 127 2 25 2 300 99% 1% ( ) 3 ( ) 2 2 36% 64% ( ) 3 ( ) 2 2 25% 75% ( ) 3 ( ) 3 ( =10.881kJ mol 1 ) ( ( ( =40.176kJ mol 1 3 ) 2 3 ) 2 2 ) [ 12] R Li RLiRLi 2 R Na 2,7- R 2,7-4 5 R 1--4- ( ) 2 2 2 2Na 2 2 ( ) 2 2 2 Li 4 5 ( ) 2 2 2 2 2 ( ) 2 2, 7-2 2 Li [13] Zn 1,1,2-2 2 8

2 c 2 2--2, 4- a 2 b 1, 3--2, 2- b c a c a Zn Zn Zn c b 2 c b 2 c b 2 2 b 1, 3--2, 3- [ 14] A 4 8 KMn 4 B 4 8 B KMn 4 A B 4 9 D ABD AB KMn 4 AB A 2 A B 2-D 1- A 2 2 2 2 2 3 2 A : 2 2 2 2 B D: 2 2 2 2 2 a a a 1. (1) 2 2 ( ) 2 9

(2) 2 2 2 2 (3) ( ) 2 2 (4) 3 2 3 (5) 2 5 (6) 2. (1) 2, 3, 7--5- (2) 2, 4--4- (3) (4) 2--6-[3.5] (5) 6-[3.2.2] (6) [2.1.0] 3. (1) 2, 2-, 2-, (2),, 2,3- (3), 2-, 2-4. (1) -1--4- (2) -1--4- (3) (4) -1--2-5. (1) (2)( 2 5 ) 3 (3) ( 2 5 ) 2 (4) 2 5 2 6. 2 7. 2 2 (1) (2) X X 8. 2,2,4- ( 14.05.1) 9. 10. 10

1.(1) 2, 4--3- (2) 3--3--6- (3) 2--3- (4) 1, 2--4- (5) 1, 5--6-[2.4] (6) 3, 7, 7-[4.1.0] 2. (1) 2 2 2 5 (2) 2 2 2 2 5 (3) 2 ( ) 3 (4) ( ) 3 2 ( ) 2 (5) (6) 3. (1)>2->2, 2- () (2) >>2, 3- () (3) 2->2-> () 4. (1) 3 e a a 3 e a e e a e a e 11

5. (2)>(3)>(4)>(1) (3 > 2 > 1 > ) 6. 2 2 2 7.(1) 2 2 2 (2) 8. ( ) 2 2 ( ) 2 ( ) 3 2 ( ) 3 ( ) 2 2 2 (15 1) : (2 4.0) : ( ) 3 2 ( ) 2 (1 5.1) 9. 2 2 2 2 2 2 2 2 2 2 2 2 2 2 10. ( 6 5 ) 3 ( 6 5 ) 3 2( 6 5 ) 3 2 2( 6 5 ) 3 ( 6 5 ) 3 ( 6 5 ) 3 12

1. () E-Z Z Ea. b. c. 2. (1) ( > > 2 N 2 > NR 2 2 > R> > R 3 > R 2 > 2 R > ) s p sp 2 120σ σ p π π σ π (2) ( ) s p sp 180σ p p π π σ π σ (3) p 1 2 3 4 2 3 p p π π-π π 19

3. (1) E E Nu E E Nu E E Nu Nu Nu E Nu 20 Nu Markovnikov( ) ( F 2 F 2 (N) 2 (N) 2 ) Ar 3 >Ar 2 > Ar 2 ~ R 3 > 2 2 > R 2 >R 2 > a. b. c. (2) R R 2R R R R 2 R R 2 R 2 2 2 2 2 3 2 4 RS I (3) sp s 50% NRR RS (4)

1,2-1,4-1,4- E 4 3 2 1 Nu E 4 4 3 2 1 3 2 1 Nu E Nu 4 3 2 1 E 1 2 4 2 1,2-4 1,4-4. (1) 2 /Pt, Ni 2 X X X 2 2 X X I 2 () 2 S 4 X 2 () S 3 2 21

2 / 3 P 4 3 300, 7MPa B 2 6 ( 3 2 2 ), 2 B 2 3 2 2 2 2 Ag 2 250 2 u 370 2 R 3 2 R 2-2 KMn 4 2 3 Zn/ 2 2 n 3 2 2 2 2 500 2 /Mn 2 2 400 3 N 3 2 2, 470 2 N (2) 2 R R' 2 2 () 2 /Pt, Pd Ni 2 Lindlar Na N 3 (l) R 2 2 R' R R' R R' () 22

NaN 2, Na Na Na Ag(N 3 ) 2 N 3 Ag u(n 3 ) 2 u X X X X 2 X 2 X 2 X 2 2 2 2 2 X 2 2 S 4 gs 4 2 X 2 X () X X R K,, R/ 2 S 4 KMn 4 2 R 2 R 2 (3) 2 2 2 2 2 2 X 2 1, 4 1, 2-1, 4-2 2 2 X 1, 2-1, 4-2 2 n 2 2 X 2 n 2 2 2 n 23

5. (1) Wittig (2) X R 2 2 R 2 2 X Al 2 3, 2 S 4,, R R 2 2 R 2 X R 2 Ph 3 P R' 2 R 2 R' 2 (RR ) R (3) a 2 2 a() 2 K R 2 X 2 R' R R' KX K RXXR' R R' KX M R'X R R' (MKNaLi) u 2 2 N 4 2 2 2 2 2 Lindlar 2 () 2 2 2 Al 2 3, 2 S 4, 2 2 24 [ 1] 2 2 2 5 (1) (2) 3 ( ) 3 ( ) 2 3 7 n (1) 2 > ( ) 3 > E (E)-4, 4--3- -2- (2) 2 > 2 2, ( ) 2 > 2, E (E)-2- -3--4--3--5- [ 2] (1) ( ) 2 2 2 S 4

(2) (3) (1 mol) (4) 2 S 4 /gs 4 (5) ( ) 2 (6) 22 (7) 2 Ag 2 (8) 2/ (9) KMn 4 (10) KMn 4 (11) 3 Zn/ 2 2 S 4 (1) ( ) 2 2 ( ) 2 S 3 (2) (3) (4) 1 mol gs 4 / 2 (5) ( ) 2 (6) 3 2 2 ( ) 2 Ag/ 2 (7) 2 2 (8) 2 3 P 4 / 2, 3 (9) KMn 4 2 () (10) KMn 4 2 25

(11) 3 Zn/ 2 [ 3] B 2 6 (1) 2 2? 2 2,? (2) 3 2 2 2 2 (3) 2 2 (4) 2 2 500 (5) (6) (7) NaN 2? 2 N 3? 3 ( 2 ) 3 AgN 3 N3 2 (8) 2 2 (1 mol) (9) 2 2 2 (1 mol) (10) ( 2 ) 3 2 (1 mol) (1) 2 2 2 3 B 2 2 2 () (2) 2 2 2 2 ( ) (3) ( ) 2 (4) 2 (α-) 26

(5) (Diels-Alder ) (6) Na 2 () (7) ( 2 ) 3 Ag () (8) 2 2 2 (1,2-) (1,2-,) (1,4-,) (9) 2 2 () (10) ( 2 ) 3 () [ 4] (1) 2 2 (2) 2 (3) 2 2 (4) ( ) 2 2 (4)>(2)>(1)>(3) > 2 > (4)>(2)>(1)>(3) [ 5] (1) (2) ( 2 ) 4 ( 2 ) 3 ( 2 ) 2 (1) (2) ( 2 ) 4 ( 2 ) 3 ( 2 ) 2 2 / 4 2 / 4 ( 2 ) 3 ( 2 ) 2 [ 6] KMn 4 Ag(N 3 ) 2 (1) a b (2) a 2 2 2 2 27

b (1) b>a (2) b>a (1)b σ -π (2) b a [ 7] A. ( ) 3 B. () 2. 2 A>B>>D D. 9 σ p 6 σ 3 σ σ A>B>>D [ 8] (1) 2 (2) (3) (4) (1) Diels-Alder 2 2 (2) (70%) (30%) Diels-Alder 2 1,4 (3) 28

100% Diels-Alder 1 (4) () Diels-Alder ( R N N 2) [ 9] 3--1- () 2 () 2 2 ( ) 2 ( ) 2 2 ( ) 2 2 - ( ) 2 ( ) 2 2 [ 10] (1) 2 2 ( ) 2 - (2) (3) 2 2 2 2 ( ) 2 2 (4) 2 (1) 2 S 4-2 2 2 2 (2) 2 K KMn 4-29

(3) 2 2 5 Na, 2 5 KMn 4-2 2 2 2 (4) [11] KMn 4 2 2 2 S 4, 2-2 Diels-Alder (1) (2) 2 (3) 3 3 (4) 3 (1) (2) 3 (3) 3 3 3 3 (4) 3 3 [ 12] A B D E F A Zn B Zn 2 B KMn 4 2 2 2 30

B Li D 2D ui E E F A 2 2 B 2 2 2 2 2 D 2 2 2 Li E ( 2 2 2 ) 2 uli F ( 2 ) 6 [ 13] 8 14 1mol Zn/ 2 2 2 8 14 4 2 1mol 1 2 2 2 2 [14] A 7 12 KMn 4-2 A BB K- 2 5 2 DD K- 2 5 EE KMn 4-2 2 2 3 Zn/ 2 ( 2 ) 4 A A 2 (A) 2 KMn 4 2 KMn 4 2 2 (B) K 2 5 () 3 Zn/ 2 2 (D) K 2 5 ( 2 ) 4 ( 2 ) 2 [15] (1) F 3 2 (2) 2 KMn 4 2 31

(3) (1) F 3 2 F 3 2 2 F 3 F 3 2 2 (2) 2 2 F 3 p 2 2 (3) 2 β p 2 2 [16] ( 2 ) 1--1,2-1- -1--2-2 2 2 2 2 2 [17] ( 6 5 6 5 )1- NBS( 4 17% 3--1-44%-1--2-39%-1--2- NBS 2 N ) N 2 2 N 32

2 6 5 6 5 1- ( 2 ) 4 2 2 ( 2 ) 4 2 ( 2 ) 4 ( 2 ) 4 2 ( 2 ) 4 2 2 17% 44% 39% [ 18] A 3 6 2 B( 3 6 2 ) ( 3 5 ) 2 5 MgI D( 5 10 )D NBS E( 5 9 ) E K- 2 5 F( 5 8 )F ( A G 2 B 2 2 2 A 2 2 2 2 ) Diels-Alder G 2 MgI NBS K 2 5 2 2 2 D 2 2 E F G ABF A A B A 1A F Diels-Alder F F A A [19] pk a 2 >35 4 >49 17N9 5 (1) Na (2) Li (3) Na 33

(4) NaN (5) Na 3 (1) 3 Na (2) Li 4 (3) Na 2 (4) (5) 3 Na [20] 1,4-3 α - 1,4-3 2 2 2 2 2 2 2 2 2 2 2 2 1,4- α - 1. (1) ( 2 ) 2 2 (2) 2 (3) ( ) 3 2 2 (4) 2 2 2 2 (5) 2 2 34 2 (6) 2. (1) 2, 3, 4--2- (2) E-3--4--2- (3) (4) 2, 2, 5--3- (5) 8--[3.2.1]-6- (6) 1--5- (7) (Z)-3--4--1, 3--5- (8) (2E, 5Z)-6--2, 5-3. 1-

(1) 2 S 4 (2) (3) (4) B 2 6 2 (5) (6) 2 / 4 4. (1) 2 2 KMn 4 (2) ( ) 2 KMn 4 (, ) (3) 2 2 2 5 3 Zn/ 2 (4) 3 Zn, 2 (5) R 5. (1) 2, N 4 u 2 45 ~ 60 (2) 2 (3) (4) (5) 6. (1) 2 (2) 2 2 (3) (4) 2 2 (5) 2 2 7. (1) / (2) 6 10 1mol 2 KMn 4 (3) / 8. 9. () 35

( ) 2 2 S 4 2 (3 ) 3 2 2 ( ) 3 ( ) 2 10. (1) 2 2 2 (2) ( ) 2 2 ( ) 3 2 ( ) 2 (3) 2 2 2 ( 1-) (4) 2 2 () 2 11. 23 46 23 48 / ( 2 ) 7 ( 2 ) 12 1. (1) 2--1- (2) 3- (3) 2, 2--3- (4) 3--1, 6- (5) 2, 3--1, 3- (6) (ZE)-2,4- ( ) 2. (1)( ) 2 ( )( ) 2 2 5 (2) 2 5 (3) 2 ( ) 2 (4) ( ) 3 ( ) 2 (5) 2 5 (6) 2 2 2 (7) 2 3 7 -n (8) 2 3 3. (1) (2) S 3 (3) (4) (5) (6) 4. (1) 2 2 5 (2) ( ) 2 ()() (3) 2 2 2 3 7 -n 36

(4) 2 2 2 (5) 5. (1) 2 2 (2) (3) (4) (5) 6. (5)>(1)>(4)>(3)>(2) 7. (1) 2 ( ) 2 (2) (3) 2 2 8. ( ) 3 ( ) 2 2 ( ) 3 ( ) 3 9. ( ) 2 2 ( ) 3 ( ) 2 2 ( ) 3 2 ( ) 3 ( ) 2 ( ) 3 2 2 2 10. (1) 2 500 2 2 2 / 4 2 2 2 S 4 (2) 2 ( ) 3 2 2 () 2 ( ) 3 ( ) 2 Ni ( ) 3 2 ( ) 2 2 (3) 2 2 2 2 2 Na 2 5 2 2 2 5 37

(4) 2 2 2S 4 2 () 2 11. ( 2 ) 7 ( 2 ) 12 38

1. (1) ( omp) S 3 N N 2 2 S 3 2 2 1--5--2-2 N N 2 2--6- N 2 3--5- (2) 17 α α 8 1 β β α α β β 7 6 5 4 2 3 46

α- β - N 2 S 3 N 2 1, 5- α γ α 8 9 1 β β β β 7 6 2 3 α γ α 5 10 4 2 (1) sp 2 σ p π (2) ( 6 5 2 ) (sp 2 ) p π p (3) sp 2 σ p p π π 3. (1) ArR 2 KMn 4 Ar α- α- 47

(2) 2, V 2 5 400 X 2 ( 2, 2 ) FeX 3 X N 2 N 3 2 S 4 2 S 4 S 3 2 Al 3 2 2 Al 3 ( ) 2 R Al 3 R ( ) 2 Al 3 (3) 3 2, Ni 3 2 hν 6 6 6 (4) π π π σ (σ ) () E E E E (5) 48

a. ( 6 0 % ), NR 2, NR, N 2,, NR, R, R,, 2 5, ( ) 2, ( ) 3, Ar, 2, 2, 2 2 R, F ( ),, I ( 2 ) () ( ) () b. ( 40%) () N 3 S 3,, R,, R, N 2, NR 3, N 2, F 3, 3, N, ( 3) () ( ) a. b. (6) r 3, 10~15 2, V 2 5 K 2 S 4 385~390 N 2 [] N 2 [] N 2 [] 49

X 2 ( 2, 2 ) FeX 3 N 2 N 3 2 S 4 S 3 2 S 4 60 2 165 2S4 2 S 4 165 S 3 2 2 2 Fe 3 K, 200~220 Al 3, S 2 Al 3, 6 5 N 2 (67%) (90%) Na, N 3 1, 4 2 /Pd,, Na g, 2 5 1, 2, 3, 4 2, Pt, (7) p α-β - α-α a. α α (4 ) β (2 ) α (1 ) b. 50

α β α 4. (1) π π (2) (4n2) sp 2 (4n2) π (4n2) π (4n2)π (4n2)π S N 1 7 6 2 3 4 5 5. (1) Ni() 2 [( 6 5 ) 3 P] 2 60~70, 1520kPa 6 6 600 6 6 ( 2 ) 5 2 6 5 (2) 51

Al 3 6 6 RX 6 5 R(R ) Zn 2 6 6 6 5 2 (3) Na 6 5 X RX 6 5 R R R 6 5 6 5 6 5 MgX (4) RX 6 5 R Zn g 6 5 6 5 2 2 NN 2 6 5 6 5 2 6 5 R 2, Ni 6 5 2 2 R [ 1] 6 5 (1) (2) ( ) 2 2 6 5 6 5 (3) (4) N 2 S 3 (5) (6) 2 2 (1) -1, 2- (2) 2--3- (3) 4--2- (4) 8--1- (5) 3--4- (6) [2] N (1) N 2 (2) (3) 52

(4) N 2 (5) N 2 (6) N 2 N 2 (7) (8) (9) S 3 (10) N (1) (2) (3) N 2 (4) (5) N 2 (6) N 2 N 2 N 2 (7) (8) (9) S 3 (10) (1) (2) 2 4 6 (3) N N N (4) (5)(6) 2 4 6 (7)(8) α 53

αβα (9)(10)αβ 5 8 [ 3] () (1) ( ) 2 2? (2) ( ) 2 ( ) 2 2 Al 3 KMn? 4,? 2 (3) ( ) 3 Al 3?? Zn g (4) 2 Fe 3?? (5) 2 N N 3 2 S 4? (1) ( ) 2 2 ( ) 2 ( ) 2 (2) ( ) 2 2 Al 3 KMn4, 2 ( ) 3 ( ) 3 ( ) 3 ( ) 3 ( ) 3 (3) Al 3 Zn g ( ) 2-2 ( ) 2 (4) 2 Fe 3 (5) 2 N N 3 2 S 4 2 N N 2 π () 4 4,4'- 54

[ 4] N 3 (1) 2 N 2 N 2 S 2 2 4 N 2 N 2 N 2 R N 2 (2) RX Al 3 R (3) 2 Al 3 (4) 2 Al 3 2 2 (1) 2 N 2 N 3 2 S 2 N 2 N 2 4 4 (2) Al 3 (3) Al 3 Fridel-rafts(-) [5] () (1) (2) (3) (1) (2) (3) [ 6] (1) 2 (2) 55

(3) 1,3,5,7- KMn 4 4 8 8 8 K 2K 8 2 8 () (1) π (2) (3) [7] A( 9 8 )A B( 9 12 ) B ( 8 6 4 ) D( 8 4 3 ) A EE 2- ABDE A. B. 2. D. E. u(n 3 ) 2 u 2 2 [] 56

2 2 A 9 8 2n 2 2 9 2 8 = = = 6 6 4 2 2 ( 4) A B 8 6 4 A [8] 4 ( ) (1) N2 (2) ( ) 2 N 2 (3) ( ) 3 (4) 2 N ( ) N 2 (5) 2N (6) N 2 (1) 2 S 4 N 3 2 S 4 N 2 3 N2 S 3 S 3 N 2 S 3 N 2 S 3 (2) 2 ( ) 2 Al 3 N 3 2 S 4 57

2 N ( ) 2 2 Fe 2 N ( ) 2 (3) ( ) 3 Al 3 KMn 4, 3 ( ) 3 ( ) 3 (4) 2 Al 3 2 2 6 6 N 3 Al 3 2 S 4 2 N N 2 2 N N 2 6 6 2 2 (5) 2 KMn 4, 3 S 2 6 6 Al 3 N 3, 2 S 4 2 N 58

N 2 N 2 (6) N 3 2 S 4 2 Fe 3 α- 4--1- [ 9] (1) (2) (3) (4) (5) (6) (7) (8) (9) 65 (10) (11) 65 65 (1) (3) (5) (7) (10) ckel sp 2 sp 2 (11) (9) π 4n 2(2) (4)(6)(8)π 2 π π 0 2 π 1 π [10] 59

σ σ σ [11] (1) 45 250 (2) 14 22 (3) (1) (2) 6 6 2 ( ) 3 ( ) 3 ( ) 3 ( ) 3 ( ) 3 ( ) 3 (3) ( ) 3 2 ( ) 3 2 2 ( ) 3 2 2 ( ) 3 2 2 ( ) 3 ( ) 2 2 ( ) 2 2 5 60

[12] (1) 2 2 2 2 2 2 N 2 N 2 N 3 32% 59% N 2 5 69% 28% (2) N 2 I KI Ti(F 3 ) 3 2 (3) 2 2 2 2 KI Ti(F 3 ) 3 2 I (1) (a) (b) (b) π π N N 2 N 2 N 2 2 3 3 (a) (b) (2) Ti(F ) Ti(F 3 ) 3 Ti(F 3 ) 3 Ti(F 3 ) 3 2KI 2 I (3) Ti(F 3 ) 3 [13] () (1) BF 3 60? 61

(2) 2 2 Al3 2? ( ) 2 (3) Zn 2 ( ) 2? (4) K 2 r 2 7 2 S 4? (5) r 3, 2 2?? ( ) 2 ( ) 2 ( ) 2 (6) N 2 N 2 N 2 Na? ( ) 2 N 2 (7) 2 2 F BF 3 20? 2 2 2 ( ) 2 (8) 2 S 4? (1) (2) ( ) 2 2 2 (3) (4) ( ) 2 2 (5) 2 2 2 (6) 2 Fe 3 2 500 N 2 62

(7) 2 2 (8) 2 2 3 [14] 2 2 ( ) 3 (1) 2 (2) R (1) 2 S 4 2 2 ( ) 3 3 2 3 2 R 2 2 2 ( ) 2 2 2 (2) 2 R 2 R R 2 2 R R R 2 2 R R 63

1. 2 5 3 (1) (2) (3) 2 2 (4) (5) (6) N 2 ( ) 2 ( ) 2 (7) (8) (9) (10) N 2 2 N (11) 2. (1) (2) (3) 1,3--1, 4- (4) (Z) -1,2- (5) 3-() (6) (7) 4--2, 3- (8) 2--6- (9) 4,4 - (10) α- (11) 3--2- (12) 9,10-3. (1) 2 Al 3 N 3? 2 S? 4 (2) ( ) 2 2 (3) Al 3? Al 3 2 S? 4? 64

(4) Al 3 ( 2 ) 2? (5) Al 3 2 2 2? (6)? Al 3 2 5 KMn 4? (7) 2 S 4 160? N 3 2 S 4?? (8) Al 3? 2 N 2 (9) 2 S?? Al 3 4? N 3 2 S 4 60 (10)? 2 Fe?? 4. 3 2 2 (1) (2) (3) N 2 (4) 2 (5) (6) (7) (8) 2 N 2 5. (1) (2) 2 4 2 (3) KMn 4 K 2 r 2 7, 2 N 2 N 2 65

6. (1) () 3 2 S 4 Al 3 3 2 (2) 3 4 Friedel-rafts 4 (3) NaN 3 2 N 3 - (4) 6 6 Zn 3 7. B( 10 14 ) ( 10 13 ) B 8 6 4 8 5 4 N 2 B 8. 10 14 9. - 1,2,3-10. (1) (2) (3) (4) (5) (6) (7) (8) (9) (10) 2 1. (1) 2-2--1,3,5- (2) (3) 1,4--2- (4) 1,1- (5) (6) (7) 9--10- (8) 1--5- (9) (10) 2--4 - (11) 4,4-66

2. (1) 2 (2) 2 (3) F (4) (5) 2 2 (6) N 2 (7) (8) N 2 S 3 (10) 2 N N 2 (9) 2 N N 2 (11) 2 (12) 2 3. (1) 2 (2) S 3 N 2 (3) ( ) 3 ( ) 3 (4) (5) (6) 2 2 67

(7) S 3 N 2 N 2 S 3 S 3 (160 β (8) 2 (9) N 2 2 N N 2 (10) S 3 S 3 S 3 4. (1) 2, Fe hν, 2 2 2 5 2 5 2 (2) 2 2 Al 3 2 Fe 2 hν K (3) Al 3 ( ) 2 ( ) 2 2 hν ( ) 2 N (4) 3 3 2 N 2 3 2 S 4 hν 2 ( ) 2 2 N 2 2 N Al 2 3 (5) 2 S 4 2 Fe 3 3 S 3 S 3 2 2 2 2 Al 5 3 hν (6) K 68

2 F (7) 2 S 4 N 3 S 3 3 2 S 4 3 S 3 3 3 KMn 4 N 2 2 N 2 N (8) 2, hν KN 3 2 2 2 5. (1) 2 (2) ( 2) (12 ) (3 ) (3) N 2 6. (1) 3 3 3 2 S 4 3 S 3 4 3 Al 3 Al4 3 3 2 2 3 3 (2) Al 3 3 Al 4 3 3 (3) N 2-3 3 2 N 2 3 N 3 3-2 3 (4) Zn 3 3 69

2 3 Zn Zn 2 2 3 3 3 7. ( ) 2 8. R α- 3 ( ) 3 9. ( ) 3 (3)2 2 2 Al 3 F ( ) 3 ( ) 3 ( ) 2 2 F ( ) 3 ( ) 2 10. (1) (4) (5) (7) (10) 2 70

1. (1 ) (2 ) (3 ) 2. X δ X δ X NaMgLi (1) RX Nu RNu X R () R' R R' (1 RX2 3 ) R'R () N 3 RN 2 () R' RX R' N I R N () RI () R' R (, ) AgN 3 R N 2 (, AgX) AgX S RS () R'S RSR' () RX S N 1 S N 2S N 1 S N 2 X NuRX 81

(2) B X X RX E1 E2E1 E2 δ X E1 E2 (3) RX Grignard() RX Mg RMgX RX RMgX RMgX RX Li 2RLi ui R 2 uli R'X (4) 0 RLi R Y R'X R MgXY ( Y 2, R, R, N 3, R ) R' R R MgX () 2RX 2Na R 2 uli LiI R' Ru LiX RX B δ 3 R (R'X) Zn/ 2/Pd LiAl 4 R R 2NaX R R R 3. RX (1) X X 82

(2) X X 4. R X 2 RX X X, X 2, X X R X RX 2 RX RIRX(, ) NaI RI NaX(, ) [ 1] (1) 2 (2) 2 2 F (3) 2 2 2 2 (4) 2 ( ) 2 2 5 (5) 2 2 (6) (7) I (8) 2 5 (9) 2--4- (10) (11) - (12) 1--2--4- (13) 3--5- (14) 3--4--1- (1) 2 2- (2) 2 2--4,4,6- (3) F 2- -3--4--4- (4) 4--2--1-2 5 83

(5) 3--6--2--14- (6) 1 1--4--3- (7) I -1--4- (8) 3,5- (9) 2 2 (10) 2 2 2 (11) (12) 2 ( ) 2 2 5 2 5 (13) (14) 2 [ 2] 2- (1) Na (2) K (3) Mg (4) (3)D 2 (5) 2 Pt (6) NaI (7) 6 6 Al 3 (8) Na (9) NaN (10) N 3 (1) 2 (2) 2 RX (3) 2 () Mg (4) 2 (5) 2 2 (6) I 2 D I (7) - 2 5 (8) 2 (9) 2 (10) 2 N [ 3] N 2 84

(1) 6 5 6 5 (2) 2 I N (3) ( ) 2 I 2 (4) 2 2 LiAl 4 (5) ( ) 3 2 5 (6) 2 K (7) Na (8) Al 3 (9) N 2 Na / (10) Mg (1) 6 5 6 5 (2) 2 N (3) ( ) 2 (4) RX 2 (5) ( ) 3 2 5 (6) (7) 2 (8) - (9) () 3 N 2 (10) 3 Mg [ 4] (1) AgN 3 ( ) 2 A. B. 85

. 2 D. 2 2 (2) S N 2 E2 ( ) 2 2 2 A. B. 2 2 2 2. D. (3) S N1 ( ) 2 2 2 2 2 2 A. >>> B. >>>. >>> D. >>> (4) S N2 ( ) ( ) A. 2 B. ( ) 2. 2 D. 2 2 2 (5) NaI/( ) I 2 2 I A. B.. D. (6) ( ) A. B.. D. (7) Na 2 5 ( ) N 2 F N 2 A. B.. D. F 86

(8) ( ) A. 2 B. 2. 2 2 2 D. 2 2 2 (1) RX AgN 3 ~3 >2 >1 >A.2 B.1.D.1 (2) RX - BD A A (3) S N 1 2 1 1 2 >>> B (4) S N 2 S N 2 D(1 RX ) B (3 RX ) (5) A BD () (6) AB D RX (7) A (8) B [ 5] (1) ( ) 3 2 ( 1 RX) S N 2 (2) R ( ) 3 >( ) 2 > 2 > (3) R 2 R 2 KI (4) S N 2 S N 1 1-(S N 2 ) Na 2- -2-(S N 1) (5) S N 1 E1 (6) ( ) 3 K (7) 2 I I D 3 2 I DI (8) 2 2 2 2 2 (1) ( ) 3 () ( ) 3 2 1 RX S N2 (2) sp 2 R ( ) 3 X 109 28'(sp 3 ) 87

( ) 3 120 (sp 2 ) () (3) I R RII RI R I 88 2 R 2 I R 2 I R 2 I (4) S N 2 S N 1 (5) 3 RX S N1 E1 (6) 3 RX S N1 3 RX E2 (7) E2 D D D (8) (Y)RMgX Y R MgXY R 2 Mg R 2 R 2 2 R [ 6] (1) (2) (3) 1--1-1--2- (4) 1,1,1- (5) 3--2-4--2-5--2- (6) (7) 1,2- (1) ( 2 ) 3 NaI/ Na (2) ( 2 ) 3 ( 2 ) 3 F (3) 2 AgN 3 / 2 2 (4) 2 I AgN 3 / 2 3 (5) AgN 3 / 2 ( 2 ) 2 2 (6) AgN 3 / 2 2 / 4 KMn 4

(7) KMn 4 1,2- AgN 3 / 2 [ 7] 1-() (1) (2) 1,2- (3) 2,2- (4) 1,1,2,2- (5) 1, 3--2- (6) 2,3--1- (7) (8) (9) (10) (11) (12) (1) β K, Et 2, 500 2 2 2 2 2 (2) X 2 2 2 K, Et 2 2, 4 3 2 (3) X 2 2 K, Et 2 2 3 2 NaN 2 2 3 2 (4) X 2 K, Et 2 2 NaN 2 2 2 3 2 2 (5) 2 / 2 2, 2 2 2 2 2 ( δ δ ) (6) X 2 2 2 2 2, 4 (7) N (8) RX 2 2 2 NaN N 3 2 2 N 2 2 2 2 N 2 (9) N 2 2 2 K, Et N 3 2 2 2, 4 3 N 2 3 (10) 2 2 2 2 KMn 4 (11) 2 2 NaN 2 2 Mg 2 2 N 3 2 2 Mg 2 2 2 89

2 3 3 2 2 (12) RXR 2 2 2 2 2 2 2 2 2 2 K 3 [ 8] (1) 2 2 2 2 ( 2 ) 3 2 (2) 2 2 2 2 (3) (4) 6 5 (5) 2 ( ) 2 (6) 2 2 2 (7) ( ) 2 2 2 (8) 2 2 2 2 2 2 N 2 (9) ( 2 ) 4 (10) 2 2 2 ( ) 2 (1) 2 2 2 Na ( 2 ) 3 2 2 ( 2 ) 3 2 Lindlar (2) 2 2 2 K Et 2 NBS 2 2 (A) 6 5 Li 6 5 Li ui A ( 6 5 ) 2 uli 2 (3) (4) 90 K, Et NBS 2, 4 6 5

2, 4 K, 2 2, 4 NBS 2, 4 (5) 2 (6) α- 2 NBS ( ) 2 2 K, 2, 4 ( ) 2 2 2 2 (7) 2 K ( ) 2 ( ) 2 2 2 2 2 2 2 (8) RX N 2 NaN 2 Na ( 2 ) 3 Na ( 2 ) 3 2 Lindlar ( 2 ) 3 2 ( 2 ) 3 N 2 N 3 3 ( 2 ) 3 (9) K, Et 3 3 2 2 2 Na 2 2 2 2 2 2 3 ( 2 ) 3 2 Lindlar NaN 3 ( 2 ) 4 N 3 ( 2 ) 4 (10) (Williamson ) Na 2 2 3 () 2 2 2 () 3 Na 2 2 ( ) 2 [ 9] (1) A BB AB (2) AB 4 9 A Na 4 10 B 91

Na 4 8 Na 4 10 4 8 AB (3) 8 9 AB AgN 3 / 2 A B B KMn 4 AB (4) A 2 BB AB (5) 6 13 I K/ 2 ( ) 2 (6) A 7 8 B DB D E( 7 6 2 )E KN F( 8 7 2 ) A~F (7) A BA KMn 4 12-A Na D D E FE F E F A~F (8) AB 6 4 N 2 AB K 6 4 N 2 AB (1) B B 2 A 2 2 (2) Na RX 1 RX 2 RX 3 RX A 2 2 2 B ( ) 3 2 5 (3) AgN 3 / 2 3 RX RX 1 RX 2 RX RX B A 2 2 B 2 3 2 2 3 (4) B B B A 2 A (5) K/ 2 ( ) 2 I 2 ( ) 2 92

(6) A A A E BD KN E 2 A., B. 2,., D. E. 2 F. (7) A KMn 4 1,2- A A Na A αa D α D EF E F E F F A. 2 B. 2. () 2 D. 2 E. () 2 F. 2 2 2 (8) AB N 2 AB N 2 A. N 2 B. N 2. N 2 1. 2. 6 5 3 2 2 (1) (2) F (3) 2 (4) 2--1-(2-) (5) 2,6--4- (6) 1,2,3,4,5,5-3. (1) Na Et A NBS B Na 2 (2) ( A 2, 4 3) 2 ( ) 2 (3) ( ) 3 80%Et, 20% 2 A B 25 B K Et 93

Et, 25 (4) 2 ( ) 2 A B 1 mol NaS (5) 2 2 2 2 Na A B (6) (3 ) 2 K, Et (7) ( ) 3 K A B B A 3 2 2 (8) 2 2 Na 2 A B NaN D Lindlar 4. (1) 2 2 Mg Mg 2 2 Mg A, 2 B 2 ( 2 ) 2 2 A (2) ( ) 2 2 / ( ) 3 NaN B ( ) 3 N (3) 2 A 2 Mg B (4) ( ) 2 2 A ( ) 3 Na B ( ) 3 (5), g 2, A 3 2 ( ) 2 2 2 5 Na B 2 2 5 > 500 (6) 2 2 2 2 A K, Et 2 B 5. K X (1) 2--2-1-2- (2) 2--1-3--1- (3) 5--1, 3-3- (4) -2-6. S N1 (1) 1-1--2-2--2-2- (2) 1-2-1--2-2--2-1--2,2- (3) (4) 3--3--1-3--1--1-2--1--1-7. (1) 2 3 Ag 3 2 94

(2) ( ) 3 2 2, Et Ag ( ) 2 2 2 5 ( ) 2 2 ( ) 2 (3) 2, 2 8. (1) 2 2 2 ( ) 2 (2) ( ) 2 2 2 ( ) 2 (3) () 9. (1) (2) (3) 2 2 2 (4) 2 2 (5) 2 2 N 10. (1) A B 2 / 4 DA B Na E A E N E A~E (2) A B( 6 11 )A ( 6 10 )B D() E() KMn 4 ( 2 ) 4 D ( 2 ) 3 E A B 95

1. 2 2 1--2-() 2 2 1--1-() 2 () () () 2. (1) Z-2--2- (2) 5--6--2--2- (3) (4) 2 (5) (6) 3. (1) A B NBS α - (2) A RX 2 RXB ANa,Et,B( ) 2 2 ( ) 2 (3) 2 A( ) 3 B( ) 3 2 5 2 ( ) 2 (4) A ( ) 2B 2 ( ) 2 2 2 5 (5) S, A 2 2 2 2 SA R S BB S (6) β - A( ) 2 96

B( ) 2 ( ) 2 (7) A 2A B B (8) A,, A 2 2 2, Lindlar A, B 2 2 2 2,, D,, D ( 2 ) 3, ( 2 ) 3 (N) 4. (1) A 2 2 (2) A (3) A B (4) A (5) B () (6) B 5. (1) 2 ( ) > 2 2 > ( 2 ) 4 (2) 6 5 2 > 6 5 2 2 2 (3) > > (4) -2->-2-6. (1) ( 2 ) 3 <( ) 2 2 < 2 <( ) 3 (2) ( 2 ) 4 < 2 ( ) 2 <( ) 3 2 < 2 2 <( ) 2 2 (3) 6 5 2 <( 6 5 ) 2 <( 6 5 ) 3 (4) 6 5 < 6 5 2 < 2 6 5 7. (1) Ag 2 2 1,2 3 Ag 2 2 2 (2) (1) ( ) 2 2 (S N 1) 2 Et ( ) 2 2 (S N 1) 2 5 ( ) 2 (E1) (3) 2 E1 S N1 97

2 2 2 2 (E1) (S N 1) 8. (1) K, Et 2, 500 3 2 2 2 ( ) 2 2 Mg, (3 ) 2 2 Mg 2 2 2 ( 2 ) 2 ( ) 2 Na 2 (2) ( ) 2 Lindlar ( ) 2 ( ) 2 2 2 ( ) 2 ( ) 2 Na ( ) 2 2 2 ( ) 2 (3) 1() 2 2α - 2 3 X X 2 2 2 4 X X 2 5 2 2 2 500 g 2 2, Zn 2 2 2 6 2, Fe 9. (1) Mg 3 Mg (2) Williamson 2, Na Zn 2 Et 2 2 5 (3) 2 2 Al 3 hν 2 2 K, Et 2 2 2 (4) - 98

, Zn 2 2 2 2 Mg 2 (5) N RX 2 2 Al 3 2 2 Fe 2 2 2 2 2 2 N K Et NaN 10. (1) E ( 2 N) N Diels-Alder E 2 2 E AB Na AB 2 AB A B A B A α - A 2 B 2 2 2 2 D 2 2 2 (2) A B A A D ( 2 ) 3 D B E E 2DE B B 99

1. ( ) () (1 )(2 )(3 ) ( R) 2. δ δ (1) (2) (3) X Na R RNa 2 R R 2 RX ( Zn 2 ()6 R PX 3 RX P() 3 (X =, I) S 2, R S 2 (4) 109

() 2 R R R() (5) R N 3 R', R N 2 () R'R () (6) R 2 KMn 4 RRR' KMn 4 RR' 3 1 R 2 r 3 R 2 R 2 u, 2 RRR' u, 2 RR' I 4 R I 4 R R' I 3 R' I 3 AgN 3 AgI 3 () (7) Wagner-Meerwein R 1 R 4 R 2 R 3 Pinacol R 1 R 3 2 R 1 R 1 R 2 R 3 R 4 R 1 R 2 R 3 R 4 R 2 R 4 2 S 4 R 2 R 4 R 3 (8) 3. p π p-π 110

(1) Ar 2 Ar 3 p-π () (2) Fe 3 Fe 3 (3) (4) Na RX Ar Ar R Ar R RAr (5) RX Al 3 R 3 2 R () 4. δ δ (1) (2) R R 2 S 4 R R S 4 R R X RRX (I) (3) (4) aisen 111

2 2 2 200 2 (5) () 2 2 2 R 2 2 2 2 Ar R 2 2 X Ar 2 2 X Na 2 2 2 NaR, R 2 2 2 2 NaAr R 2 2 Ar N 3 2 2 N 2 [ 1] (1) 2 2 (2) (3) (4) 2 ( ) 2 (5) 2 (6) 2 2 112

2 5 (7) ( 2 ) 2 (8) 2 2 (9) (10) 2 5 (11) (12) (13) 3--2- (14) (15) 3-- (16) 1,4- (17) 4--1,2- (18) (1), 2- (2) 1- (3) 3--2- (4) (5) (6) (7) 2--3- (8) 1,2 (9) 2--4- (10) 4,5--1- (11) 2 (12) 2 2 (13) 2 (14) (15) 2 (16) 2 N N 2 (17) (18) N 2 N 2 [ 2] (1) 2 S 4 (2) 2 S 4, 130 (3) 2 S 4, 170 (4) Na (5) PI 3 (6) S 2 113

(7) Na, 2 S 4 (8) (4) (9) (4)( ) 3 (10) (2)I() 2 S 4 (1) 2 2 2 2 S 3 (2) 2 2 S 4 3 2 2 3 7 3 130 7 2 S 4 (3) 2 2 170 2 (4) 2 2 2 Na 2 2 Na 2 (5) 2 2 PI 3 2 2 I (6) S 2 2 2 S 2 2 2 (7) 2 2 Na, 2 S 4 2 2 (8) 2 2 Na 2 2 5 3 7 2 2 Na (9) 3 RX ( ) 3 ( ) 2 2 (10) () ( 2 ) 2 ( 2 ) 2 I() [ 3] (1) Na (2) Na (3) (4) 2, 2 (5) 2, S 2 (6) Fe 3 (7) 2, Ni, 200, 20266kPa (8) (9) 2 S 4 20 (10) 2 S 4 100 Na (1) 2 ( 2 ) 2 I (2) 2 (3) () (4) 114

(5) (4) (6) Fe 3 6 3 (7) (8), 2 N S 3 (9) (10) 3 S [ 4] (1) 2, (2) 2, (3) (4) 2 5 Mg, 2 (5) 2 5 (6) N 3 (7) (8) N (9) 6 5 (10) 6 5 S N 1 S N 2 (1) 2 (2) 2 (3) 2 (4) 2 2 5 (5) 2 (6) 2 N 2 2 5 (7) 2 (8) 2 N (9) 2 (10) 2 6 5 6 5 [ 5] ( ) (1) ( ) 115

A. B. 2 2. D. (2) ( ) 2 2 () 2 ( ) 3 A. >>> B. >>>. >>> D. >>> (3) ( ) 2--1-3--1-2- A. >> B. >>. >> D. >> (4) ( ) 2 A. >> B. >>. >> D. >> (5) ( ) A. 2 2 B. 2 2 2. 2 2 D. 2 2 2 (6) ( ) ( ) A. 2 B. 2 2. D. 2 2 (7) ( ) N 2 N 2 N 2 A. >>> B. >>>. >>> D. >>> (8) ( ) 116

A. B. ( ) 2. 2 D. 2 2 (9) ( ) A. 2 () B. ( ) 2 () 2. 2 2 D. ( ) 3 (10) ( ) A. ( 2 ) 2 B. 2 5 2 5. ( 2 ) 3 D. () 2 5 (1) A (2) (3) 2 >1 (4) B 3 >2 >1 (5) A (6) D>>> (7) A (8) (9) 1 (10) 1 [ 6], (1) ( 2 ) 3 2 2 S 4 (3), (2) 0 2 2 S 4 (4) 2 (5) 2 KMn 4, 2 r 3, (6) 2 25 r 3, (7) 2 25 (8) 2 ( 2 ) 33 2 Mg (1) ( 2 ) 3 2 2 2 ( 2 ) 2 (2) 2 2 ( 2 ) 2 117

(3) (4) 2 (5) (6) (7) (8) Mg 2 ( 2 ) 3 [ 7] 3 (1) 6 5 Na 2 2 A B D 2, Zn (2) N 2 I Na A 2, Fe B N 3, 2 S 4 (3) 6 5 A Na B N 3, 2 S 4 D I () (4) ( 2 2 ) 2 A NaS B (5) 2 2 A Na B 2 2 Mg 3 (6) 2 2 A B (1) A. 2 2 B. KMn 4 2 2 () 2. () D. (2) A. 118 N 2 B. N 2

() N 2 N 2 () N 2 N 2 Na (3) A. B.. () N 2 N 2 Na ( ) 2 N N 2 D. N 2 ( ) (4) A. 2 2 I (I ) B. 2 2 S (5) A. 2 () 2 () B. 2. 3 (Na ) (6) A. ( 2 ) 4 Mg () B. ( 2 ) 4. ( 2 ) 3 [ 8] (1) 1-, 2--1- (2) 1, 2-,, 2- (3),, 2--1- (4),, 2-, 3- (5), (6),, 2- (7),, (8),,, (1) 2 / 42--1-() (2) AgN 3 / 2 5 2- Ag I 4 /AgN 3I 4 1,2-I 3AgN 3 AgI (3) 2 / 4 2--1-() I 2 /Na() (4) Lucas 2-3- I 2 /Na 2- (5) KMn 4() (6) 2 / 4 2 S 4 (7) 2 S 4 119

K 2 r 7 2 S 4 (8) 2 / 2 Na 2 2 S 4 [ 9] (1) (2) (3) (4) (5) (6) (7) N 2 > > N 2,,, (1) a>b>c (2) b>a>c (3) c>b>a (4) b>a>c (5) c>b>a>d (6) >b>a>d (7) >>> [ 10] () (1) β- (2) 3--1- (3) 2--2- (4) 3--2- (5) 3--2- (6) 3--2- (7) 2--2- (8) 2--2- (9) 2- (10) 2--2,3-2 2 (1) ( ) - 2 2 S 4 Ag, 2 2 2 2 2 170 280 120 2 Fe Mg 6 6 6 5 6 5 Mg 2 2 P 3 2 2 2 K, Et 6 6 Al 6 5 2 6 5 3 6 5 2 B 2 6 2 2 6 5 2 2 2 3 6 5 2 2

(2) 6 5 (3) 3 2 6 5 2 6 5 2 2 2 2 Mg 6 5 2 Mg Mg 2 2 2 ( ) 2 Mg ( ) 2 Mg 2 ( ) 2 2 ( ) 2 2 ( ) 2 2 (4) () 2 ( ) 2 Mg ( ) 2 P 3 3 2 ( ) 2 r 3 Mg 2 () 2 Mg 3 ( ) 2 (5) (4)(4) (3 ) 2 P 3 ( ) 2 (6) (4) ( ) 2 r 3 2 S 4 ( ) 2 (7) (4) ( ) 2 2 S 4 2 (8) (7) ( ) 2 ( ) 2 ( ) 2 2 (9) (7) 2 2, Ni ( ) 2 ( ) 2 2 (10) (7) 2 2, 4 ( ) 2 ( ) 2 [ 11] (1) (2) (3) (4) (5) (6) (7) 121

(8) () Williamson 2 RX 3 RX RX ( ) 2 (1) n- 6 11 n- 6 11 ( ) 2 Na (2) 2 S 4, 2 (3) 2 2 6 5 Na 2 2 6 5 (4) P 3 (3)3 Na ( ) 3 (5) ( ) 2 2 ( ) Na ( ) 2 ( ) 2 Na (6) 2 ( ) 3 2 ( ) 3 2 2 (7) N 3 2 S 4 2 Na N 2 N 2 N 2 Na (8) 6 5 2 6 5 2 [ 12] () (1) 2-2- 3- (2) ( ) 3 2 ( ) 2 2 (3) 3-2 S 4 2-3- (4) ()( ) 3 I 122

128 (1) 2 2 ( ) 3 I, I I ( ) 3 ( ) 3 I 2 2 2 2 (2) ( ) 3 2 ( ) 3 2 3 ( ) 2 2 ( ) 2 2 (3) 2 2 2 2 S 4 β-β- (4) () S N2 I 1 I ( ) 3 I ( ) 3 (S N 2) () S N1 3 R I I ( ) 3 ( ) 3 ( ) 3 I [ 13] (1) ( 7 16 ) 7 14 (2) ( 5 10 )KMn 4( 7 12 2 ) KMn 4( ) 2 () 2 (3) ( 6 14 ) 2, 2- (4) A( 5 11 )NaB( 5 12 )B Na 2 KMn 4 2 S 4( 5 10 ) K 2 r 2 7/ 2 S 4 AB (5) A( 6 14 ) 2 S 4 Na 2 2 S 4B( 6 12 )B 2 / 4B ( 3 6 ) AB (6) A( 9 12 )Na 3NaFe 3 A B AB (7) A( 7 8 )Na 3Na A B( 7 5 3 ) AB (8) A( 7 8 ) Na I B B NaFe 3

AgN 3 /AgI AB (1) 2 2 2 ( ) 2 (2) KMn 4KMn 4, 2 (3) 2,2- ( ) 3 (4) A A B A Na 2 B B 1 2 A( ) 2 B( ) 2 ( ) 2 (5) A B B ( ) B B ( ) 2 ( ) 2 A ( ) 2 ( ) 2 (6) A A A Fe 3 A A 2 A 3 3 3 B 3 (7) A A NaNa 3 A AB A B (8) A A A Na B Na Fe 3B AgN 3 /AgI AB 129

A B B I 1. (1) 2 2 (2) 2 2 5 2 (3) (4) 2 2 2 5 (5) 2 5 2 ()() 2 (6) (7) 2 (8) (9) (10) 2., Na, (1) 2 2 2 (2) 2 A 2 () A B 2 2 2 2 /Pt B 2 2 2 S 4, (3) ( ) 2 () 2 A 2 ( ) 2 KMn 4 3 2 B (4) 6 5 A 2 N 6 5, Al 3 K 2 r 2 7, 2 S 4 (5) A B 3 130,, B Na A (6) ( ) 3 ( ) 3 3 I B I ( ) 3 I

(7) ( ) 3 (8) Na 2 S 4, 150 (3 ) A 3 ( ) 3 I A ( ) 2 Na B ( ) 2 3. (1) 1--2-1--1-1--2- (2) 2--1-3--2- (3) I S N2 S N1 I (4) ArR I RI Ar ArI R (5) 4. 2 S 4 (1) ( 2 ) 2 2 A B 2 (2) 2 2 B 2 6 2 2, A S 2 B 2 S (3) 4 2, Pt A B 100 (4) 2 2, Ag A B 2 S 4, KMn 4 (5) 2 5 A 100 (6) 2 ( 2 ) 2 2, Pt A P 3 B (7) 3 ( 2 ) 2 S 2 ( ) 2 Na A B (8) 2 5 ( ) 2 2 P 3 NaN A B (9) ( ) 3 K A 6 5 2 B (10) ( ) 2 A NaS B I (11) ( ) 2 ( 2 ) 2 2 S 4, 2 A B B K 2 r 2 7 2S 4 Na (12) A ( ) 3 B 2 ( ) 2 (13) 2S 4, A (14) ( 2 ) 4 K, Et A KMn 4 B 5. (1) ( 2 ) 3 (2) ( 2 ) 2 2 B KMn 4 Pt (4) 2 5 (3) ( 2 ) 4 2 5 2 131

(5) ( 2 ) 3 2 5 6. ( ) (1) (2) -1, 2- (3) (4) -1, 2- (5) -1, 2- (6) 1- (7) 1- (8) 2- (9) (10) 1, 3- (11) 1--1-7. (1) A( 5 12 ) MgI 4 A (2) A( 6 10 )P 3KMn 4A 4 2 A BB ( 6 10 )A AB (3) A( 8 10 2 )A I B B Na 4 10A N 3D( 8 7 8 N 3 ) ABD (4) A( 5 12 ) Na 2 S 4 I B IB AB 1. (1) 3--1- (2) 1,5--3,4- (3) -4--1- (4) 5--1,3--2- (5) 4--1,2,3- (6) 12--4 (7) 4- (8) 2--3', 4'- (9) 9- (10) 3,4-2. (1) A ()B () (2) B () (3) A () (4) A () (, ) (5) A ( ) (6) A (3 RX ) (7) A (3 ) (8) A () 3. (1) 1--1-2 π-π (2) 2 2 132

(3) RR' I RR' S N2 I R R' S N1 R R' R I RI RI R' (R1 ) R R' (R3 ) I I I (4) I S N2 6 5 S N1 ArI (5) 2 S 4, R R' R R R' R' R R' 4. (1) A ( 2 ) 2 () B 3 ( 2 ) 2 () (2) A ( 2 ) 3 () B ( 2 ) 3 (3) A B (S 2 ) (4) A 2 () B 2 () (5) A () B (6) A ( 2 ) 3 ( ) B ( 2 ) 3 (7) A ( 2 ) 2 B ( 2 ) 2 ( ) 2 (Williamson ) (8) A 2 5 ( )( 2 ) 2 B 2 5 ( )( 2 ) 2 N () (9) A( ) 3 K B( ) 3 2 6 5 (10) A( ) 2 B( ) 2 S (S ) ( ) 2 S () (11) A( ) 2 2 B( ) 2 () () 133

() 2 () (12) A Na B ( ) 2 2(3 RX ) (13) A ( ) 2 (π-π) B 2 2 ( ) 2 () () 2 (14) A 2 2 2 B 2 ( 5. (1) 2, 2 2 S 2 2 ) Mg, 3 2 Mg 2 2 2, Ag 280 2 2 (2) (1) ( 2 ) 3 2 Mg 2 S 4, 2 3 Zn, 2 3 ( 2 ) 3 (3) (1) (4) (1) 2 Mg 3 2 2 2 ( 2 ) 3 S 2 Mg 2 S 4,, 2 2 2 2 3 ( 2 ) 4 2 ( 2 ) 3 KMn 4, ( 2 ) 3 3 3 2 Mg ( 2 ) 3 2 5 (5) (3) ( 2 ) 3 2 S 4, 2 2 2 K 2 2 2 134

( 2 ) 3 Na 2 ( 2 ) 3 2 5 6. ((9)) (1) Kr 2 7 2 S 4 (2) 2 2 2 S 4 2 (3) P 3 P 3 (4) 1,2 ( 6 5 1,2 ) 6 5 2, (5) KMn 4 (6) 3 MgI 3 (7) 2 S 4 (8) (7) 2 B 2 6 2 2, (9) KMn 4 ( 2 ) 4 (10) X NBS K Et (11) (3 ) 6 5 Mg 3 6 5 6 5 7. (1) A A 3 2 ( ) 2 (2) A 2 A A 135

A () A B (3) A A A I A B Na 4 10 B 2 5 I A A A A N 3 2 5 A B 2 I N 2 2 5 D 2 N N 2 (4) A A Na 2 S 4 I IA B B 2 A 2 5 136

1. a. b. c. 2. (1) α[α] α[α] [ α] = α [ α] = α l c l d l dmc g/mld g/ml (2) (3) (4) R/SD/L Fischer d a f a c e b d d b b c a c RS () a>b>c>d d abc R abc 141

S a a d d b b c c abc R abc S DL () D/L D-L- 2 2 D- L- D- L- (5) i n (360 /n) S n (360 /n) i S n (6) (7) 2 n n 2 n /2 2 n (8) a a b b a b a b 142 (9)

[ 1] 2 5 3 (1) (2) 3 2 5 (3) (4) (5) (6) 3 2 5 2 5 (2)(3)(5)(6) S-2- (1)(4) R-2- (2)(3)(5)(6)(1)(4) R/S [ 2] (1) (2) 3 (3) (4) 143

(1) (2) (3) (4) (1)(3) [3] (1) (2) 2 2 (3) (4) 3 (5) 3 (1) (2) (5) (3) (4) [ 4] 2,4--1,3- i i [ 5] R/S 144

(1) (2) (3) (4) (5) 3 (1) 2S3R (2) 2R3R (3) 2R3R (4) R (5) 1R2R [ 6] N 2 2 N (1) (2) N 2 I 2 N N 2 2 6 5 2 5 (3) (4) 2 5 (5) (6) (7) 3 (1)(2)(3)(4) (5)(6)(7) [ 7] 3 3 (1) (2) 3 (3) 145

(4) (1) 2 2 =4 3 3 3 3 * 3 3 * 3 * 3 3 (± ) (± ) (2) (3) (4) [ 8] (1) (2R, 3S) -2--3- (2) (1S, 3R) -1--3- (3) (1R, 3R, 4S) -3--4- (4) (S) - D 3 (1) (2) I (3) (4) D [ 9] -2- Fischer Newman 146

3 2 / 2 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 Fischer 1. (1) (2) 2 (3) 2 2 (4) (5) 3 (6) 3 2. (1) (2S, 3S) -2,3- (2) -1,4- (3) -1,4- (4) -1,2-3. 147

(1) 2 5 2 5 (2) 2 5 2 5 (A) (B) (A) (B) (3) 2 5 (A) (B) (4) (A) (B) (5) 3 (A) (B) (6) (A) (B) 3 (7) 3 (A) (B) (8) 2 2 (A) (B) 4. (1) (2) 3 5 2 3 (3) 148

2 (4) (5) (6) 2 N (7) N 3 (8) (9) 5 2 (10) 5 Fischer (1) (2S3R)- 6 5 ( ) (2) (R)- (3) (S)-- (4) (2E, 4S) -3--4--2- (5) (1R2R)-1--2--1,3-2 5 (6) (7) 3 3 (8) (9) 3 2 5 (10) (11) 3 (12) 6 (1) (1S2R3S) -1,2,3-149

(2) (S) -2--1- (3) (3S5R) -3,5- (4) (R) -1,2-7 R/S ( ) 3 () () () () 8 9 A 8 12 A B( 8 18 )B A Lindar ( 8 14 ) A D( 8 14 )D ABD 1(1) (2) 2 2 2 2 (3) (4) 150

(5) (6) 2(1) (2) (3) (4) 3(1) (2) (3) (4) (5) (6) (7) (8) 4(1) (2) (3) (4) (5) (6) (7) (8) (9) (10) 5 (1) (2) 3 5 6 6 5 (3) (4) 2 6 5 N 2 -p (5) (6) 2 N 2 (7) (8) 2 (9) 3 (10) 2 2 2 2 5 2 2 2 2 151

(11) (12) 2 5 6 (1) 3 (2) (3) (4) 3 2 7()2R3S4R5R()2S3S4R5R()2S3R4S5S()2R3S4S5R()() () () 2 ()() 4 ()()()()()() 8 () () 3 3 3 () 3 () 152

9 A: 3 B: 3 : 3 3 D: 153

1. (1) (2) 1, () sp 2 2. 3. (1) (2) NNaS 3 R Na () α - α- α- (emmensen) 159

2 NN 2 /K Wolff-Kishner- Meerwein-Ponndorf-Verley NaB 4 Ag(N 3 ) 2 (Tollens) (Fehling) α- (annizzaro) 4. (1) RR' N NaS 3 R" (g) 2 R"MgX R R' N S 3 Na R R' R (R") 2 R' R R' R" R MgX R' ( N 8 ) (2) R N 2 G R R' N G 2 R' G=() G=R(Schiff) G=Ar, G= G=N N 2 (R)() G=N N 2 (3) X 2, Na R R X 3 ( ) (4) 160

Na R 2 R 2 Na R 3 R' 2 R" R 3 R" R (RR'R " ) (5) Zn g R 2 R' R' 2 NN 2 K, R 2 R' RR' 2, Pt R()R' Na NaB 4 {( ) 2 } 3 Al R()R' R()R' R 3 R 3 2 R 3 2 R Ag R N 2 3 Fehling R R 2 u 2 () 5. δ δ δ δ E ENu Nu E Nu [ 1] (1) 2 (2) 3 (3) 2 5 (4) 2 5 2 5 6 5 (5) 3 N (6) N N (7) (8) 4--2- (9) (10) (11) 2,6- (12) 161

(1) 4--1--3--2 (2) () (3),() (4) 11- (5) E- Z/E (6) (7) 2,6- (8) 2 2 (9) N N (10) (11) ( 3 ) 3 ( ) 3 (12) () [ 2] : (1) N (2) NaS 3 (3) / (4) Zn-g/ (5) / (6) (7) 2 /Na (8) / (9) NaB 4 (10) (11) (1) N N (2) NaS 3 S 3 Na (3) ( 2 ) 2 (g) (4) Zn-g (5) Mg Et 2, 3 162

(6) 2 NNN 2 NNN 2 2 Na (7) () 2 Na (8) 2 α- () NaB (9) 4 2 [( (10) 3 ) 2 ] 3 Al (11) ( 2 5 ) 3 2 5 2 5 [ 3] (1) (2) (3) 24- (4) 2 NN 2 / (5) S 2 2 S/ (6) N 3, 2 /Ni (7) Ph 3 P ( ) 2 5 (8) 2 /Na (1) 2 5 (2) 2 5 2 u 2 (3) 2 5 NN N 2 (4) 2 2 N S (5) 2 5 (6) 2 2 N 2 S (7) 2 ( ) 2 5 (8) () 2 (4)(5)(6)(8) (7) Wittig Wittig ( ) 2 5 Ph 3 P n- 4 9 Li Ph 3 P ( ) 2 5 Ph 3 P ( ) 2 5 [ 4] (1) (2) (3) N (4) 163

(5) (1) π (2) NaS 3 (3) N N N N N 164,, N, N (4) (5) α- [ 5] (1) (2) (3) 2- (4) (5) (6) (7) (8) (9) 2-3- (10) 3--2-4--2-24- (1) (Schiff) S 2 (2) (3-) 2 (3) 2- NaS 3 NaS 3

(4) 2,4-2,4- (5) 2, 4- NaS 3 (6) 4 (7) (8) Fe 3 Fe 3 (9) NaS 3 2- NaS 3 3- NaS 3 NaS 3 2-3- NaS 3 3-() 2-() (10) 4--2- Ag(N 3 ) 2 N 3 3--2- Ag(N 3 ) 2 N 3 [ 6] (1) 2 2 NNN 2 (2) 2 NaB 4 (3) N 2 N 2 (4) (5) 2 NN N 2 (6) 2 2, Ni r.t (7) 2 2, Ni (8) ( ) 3 Na (9) Na (10) I 2, Na (11) N 3 (12) Na (13) a() 2 3 4 (14) 2 (g) (15) 3 2 ( ) 3 (1) 2 2 NNN 2 2 NNN 2 (2) 2 NaB 4 2 ()3 (3) N 2 N 165

N 2 (4) 2 NN N 2 N 2 NN N 2 (5) (6) 2 2, Ni r.t. (7) 2 2, Ni 2 5 2 5 () (8) Na ( ) 3 ( ) 3 2 ( ) 3 2 (9) Na 2 2 (10) I 2, Na I 3 2 (11) N 3 ( 2 2 2 ) 2 (12) Na 2 2 (13) (14) (15) a() 2 3 4 ( 2 ) 4 (g) 2 2 ( ) 2 ( ) 3 3 2 2 ( ) 2 [ 7] (1) R g2-2 g2-2 R (2) 166

5 5 N r 3 () 2 2 5 5 N r 3 2 (3) R () R' R 2 R' u 300 Na 2 R R' R R' 2 Na 2 (4) (5) α- ( ) 2 ( ) 2 KMn 4 (3 ) 2 3 Zn-2 3 Se 2 3 Mn 2 2 S 4 Se 2 2 (6) R Al 3 R [ 8] (1) 2 2 2 2 () (2) 2 2 2 2 2 (3) 2 2 2 (4) 2 2 () (5) 2 2 2 (6) 2 2 () (7) 2 2 2 2 2 (8) 2 2 2 2 2 (9) 2 2 2 2 2 167

(1) NaB 4 NaB 4 LiAl 4 LiAl 4! (2) 2 NN 2 /K 2 NN 2 /K Zn-g- (3) Zn-g/Zn-g/ 2 NN 2 R 2 R' 2 NN 2 R NN2 R' (4) NaB 4 NaB 4 LiAl 4 (5) 2 NN 2 /K Zn-g/ (6) NaB 4 NaB 4 (7) Ag(N 3 )N 3 KMn 4 KMn 4 (8) Ag(N 3 ) 2 N 3 KMn 4 KMn 4 (9) Ag(N 3 ) 2 N 3 KMn 4 KMn 4 [9] (1) (2) 2- (3), 2 5,, (4) α-,, 2, 2 (1) (2) 2- (3) > > > 2 5 π (4) 2 > 2 > > α - α - [ 10] (1) 2 2 2 168

(2) 2 2 2 5 (3) ( ) 2 (4) 2 2 () () (5) 2 ( ) 2 ( ) 2 (6) 2 2 ( 2 2 2 ) 2 (7) 2 2 ( 2 ) 4 (1) 2 2 u 2 Pd 2 / 2 Na NaB 4 3 2 2 2 S 2 3 2 2 4 2 (Sarett) (Grignard) 2-1- 1,2-2 2 2 2 2 Mg Et 2 Mg 2 2 2 2 2 () 2 S 4 2 2 3 2 Ag/ 2 2 2 3 Mg 2 2 2 2 2 2 3 2 Et 2 2 2 Mg 2 2 () 2 S 4 2 (2) 2 2 2 2 3 KMn 4 2 Mg Et 2 2 Mg 2 5 169

α - ( ) u 2 / 2 Pd 2 2 2 2 /Ni 2 hν 2 Na 2 (3) 2 Mg Fe 3 Et 2 Mg 3 g 2 3 (2) 6 5 ( ) 2 6 5 ( ) 2 2 2 2 (4) KMn 4 2 Et 2 (Et) 2 KMn 4 Na 2 (Et) 2 3 2 2 2 2 3 2 Na 2 (5) 2 R 3 2 3 2 170

2 3 Mg Et 2 KMn 4 2 ( ) 2 () 2 Mg ( ) 2 Et 2 3 2 S 4 ( ) 2 ( ) 2 ( ) 2 Mg Zn ( ) 2 ( ) 2 Ph 3 P n- 4 9 Li ( ) 2 PPh 3 ( ) 2 PPh 3 ( ) 2 ( ) 2 ( ) Mg Wittig (Wittig ) (6) 3 Zn-2 ( 2 2 ) 2 (7) 2 2 u 2, Pd 2 3 Na 2 2 /Ni 2 2 2 Mg 2 2 2 S 2 2 2 2 3 Ag 2 2 2 ( 2 ) 5 2 5 N r 3 2 2 R 3 Mg Et 2 ( 2 ) 4 1- [ 11] (1) (Schiff) Mg 4 (2) 4 8 2 4 8 NaS 3 (3) 5 10 NaS 3 24- (1) (2) 2 2 5 (3) 2 5 2 5 171

(1)() () 4 (2) 4 8 2 4 8 NaS 3 4 2 2 (3) 5 NaS 3 R 2 5 2 5 [12] (1) AB 4 8 ; AB B A A B AB (2) 10 16, 3 4- (3) 8 8 ABA NaS 3 B NaS 3 AB (1) A 2 B 2 2 ( ) 2 () 2 (2) ( ) 2 2 2 (3) A 6 5 B 6 5 2 (1) 4 8 AB B A A R (2) 3 3 3 10 (3) 8 8 5 A () NaS 3, () 8 8 [ 13] (1) 2 (2) 172

(3) (4) (5) () N (1) Al 3 Zn-g 2 (2) 3 KMn 4 (3) 2 2 A 3 (4) 3 KMn 4 Na 2 S 4 5 5 N r 3 KN (5) () () N N [14] 2-αβ - (1) (2) N 3 (3) 2 /Ni, r.t. (4) MgI (5) Li (6) LiAl 4 (7) Na (8) ( ) 2 uli (9) 1, 3- (10) N (11) N 2 (12) NaS 3 (1) 2 N (2) N 3 (3) 2 /Ni r. t. 173

(4) MgI 2 (5) Li (6) LiAl 4 (7) (8) Na ( ) 2 uli (9) (10) N N (11) N 2 N (12) NaS 3 Na 3 S α, β- 1,4-1,2-1,4-1,2-LiAl 4 NaB 4 1,2-1,4-1, 4-(10)(11)(12) 1, 4- [15] (1) (2) (3) NNN 2 (4) (5) (7) 3 (6) N (8) 174 (9) (F 3 ) 2 () 2 (1) 2 2

(2) Mg 2 (3) 2 NNN 2 NNN 2 (4) ( 2 ) 4 LiAl (5) 4 3 3 () N (6) N 2Mg (7) 3 3 (8) Na ( 2 2 ) 2 (9) (F 3 ) 2 2 (F 3 ) 2 () 2 [ 16] (1) 2- (2) (3) (1) 2,4-2- 2, 4-2- (2) 2,4-2 5 I NaS 3 (3) NaS 3 2,4- NaS 3 a 2 a 2 a a 2 [17] (1) 2 5 ()( ) 2 (2) 2 (3) 3 ()( ) 2 (4) 2 5 (5) 3 (6) 3 2 175

(1) Mg 2 5 Et2 2 5 Mg ( ) 2 2 5 ( ) 2 3 2 5 ( ) 2 Mg (2) 3 2 hν 2 Mg Et 2 Mg 2 2 5 5 N r 3 2 2 2 3 α- β- Mg 2 2 2 2 Mg 2 2 2 (3) 3 3 Al 3 3 3 (3 ) 2 Mg 3 ( ) 2 3 (4) Al 3 2 Fe Zn-g 2 5 (5) Al 3 ( ) 2 3, Gattermann-Koch Se 2 u, Al 3 3 1mol Se 2 3 176

(6) Al 3 u, Al 3 NaB 4 2 [18] () (1) 2 2 ()( 2 ) 2 (2) ( ) 2 ( 2 ) 2 ( ) 2 2 2 (1) ( 2 ) 2 2 2 ( 2 ) 2 Et 2 3 2 NN 2 3 2 -Zn 3 ( 2 ) 2 Mg Mg( Et 2 2 ) 2 3 ()( 2 ) 2 4-3- (2) ( ) 2 ( 2 ) 2 S 2 K ( ) 2 ( 2 ) 2 (3 ) 2 2 Et 3 (3 ) 2 -Zn 2 2 ( ) 2 ( 2 ) 2 Mg Et 2 ( ) 2 ( 2 ) 3 S 2 ( ) 2 ( 2 ) 2 Mg ( ) 2 ( 2 ) 3 ( ) 2 2 2 2 3 K Et S 2 [19] (1) () (2) 177

(3) (1) Se 2 KN K () (2) 2 3 K 2 2 K Micheal Micheal α- α, β- 1, 4- KMn 4 - (3) 1. (1) (2) 3 () 2 (3) 2 ( ) 2 (4) N 2 (6) 2 N (5) 2 2 N NN N 2 178 (7) N (8) 2 (9) (10) (11) 4- (12) 9,10--2-

(13) (14) 2. (1) 2 K (2) 2 Me (3) 1mol 2 (4) Ag ( ) 2 N3 ( ) 3 (5) 3 2 Na 3 (6) Mg 2 Na (7) 2 ( 2 2 ) 2 Na (8) 2 (9) Zn-g (10) () NaS 3 2 (11) ( ) 2 2 N 2 (12) 2mol N 3. (1) (2) 2- (3) 3- (4) 3-3- 4. (1)?? (2) ( ) 2 ( ) 2 ()( ) 2 2 () ( ) 2 2? 5. (1) 2 N (2) 2 2 2 5 179

(3) 2 5 (4) 2 (5) 2 5 2 5 2 5 6. (1) (2) 1,2- (3) 1- (4) (5) 3, 4--2, 4-7. (1) A 7 12 A 2 BB 7 14 B 2 S 4 7 12 KMn 4 DD 7 14 2 D I 2 /K E I 3 E 6 10 3 A~E (2) A 6 10 NaB 4 BB 6 12 B 2 2 2 S 4 6 10 KMn 4 DD 6 10 3 D AB D (3) A 6 12 NaS 3 A B B AB (4) A 10 12 Na A 2 BB 10 14 B B I 8 7 I Na A Fe 3 2 DD 10 11 2 A~D 1. (1) (2) (3) 3,3- (4) 5,6--2--1, 4- (5) 1--2,2- (6) 2,4--2,4- (7) (8) (9) (10) 2 180

(11) (12) S 3 (13) 2 (14) NN N 2 2. (1) 2 Na 3 Me (2) 2 3 2 ( ) 2 (3) 1mol 2 Ag (4) ( ) 2 N 3 ( ) 2 3 (5) 2 Na (6) Mg 2 (7) 2 ( 2 2 ) 2 Na (8) Na 2 Zn-g (9) 2 (10) 3 NaS 3 2 S 3 Na (11) ( ) 2 2 N 2 ( ) 2 2 N N (12) 2mol N N 181

3. (1) 4 (2) 2- KMn 4 (3) 2,4- (4), 3-3- 4. (1) Ag(N 3 ) 2 N 3 (2) 2,4-( ) 2 2 ( ) 2 () ( ) 2 2 /Pd- r.t. ( ) 2 2 ( ) 2 2 /Ni ( ) 2 2 () ( ) 2 NaB 4 (3 ) 2 () 5. (1) Me (Me) 2 2 S 4 N 3 2 N (Me) 2 3 2 N (2) n- 3 7 2 S 4 3 2 3 n- 3 7 Zn- 2 S 2 Mg/Et 2 2 n- 3 7 Mg n- 3 7 () 2 S 4 2 5 2 Wittig (3) g 2 3 NaB 4 2 5 S 2 2 5 Mg Et 2 2 5 Mg 2 5 () KMn 4 2 5 Wittig 2 5 Ph 3 P 2 5 PPh 3 n- 4 9 Li PPh 3 3 KMn 3 2 5 () 4 3 Pd 2 / 2 2 5 u 2 182

Na 2 /Ni 2 5 2 2 2 S 4 3 Pd 2 / 2 u 2 Mg Mg 3 ()() Zn Pd 2 / 2 u 2 Wittig Mg 4 (Me) 2 3 Zn- 2 2 (Me) 2 NaB 4 3 2 2 () 2 () 5 Wittig 2 5 2 2 4 9 Na 4 9 5 5 N r 3 n- n- 2 Mg n- 3 7 2 n- 3 7 3 7 -n 2 5 2 5 Al 2 3 2 4 9 Ph 3P n- 4 9 Li n- n- 3 7 PPh 3 n- 3 7 6.1 2 5 n- 2 3 7 3 7 -n ( n- 3 7 ) 2 2 5 2 5 5 5 N r 3 Na K Et 2 -Ni r.t. KMn 4 S 2 Al 3 n- 3 7 n- 3 7 2 n- 3 7 2 NN 2 3 7 -n 4 9 -n K - g-zn/ K/ 2 NN 2 2 n- 3 7 Mg () 3 7 -n Et 2, 3 4 9 -n α- 2 -Ni 183

2 2 hν Mg 2 Et2 2 Mg Se 2 2 S 4 2 2 Mg 2 2 2 Na ()() Mg Wittig 1,2- Mg 2 ()() KN K () NaB 4 ()() 2 Ph 3 (3) NaB 4 ( 2 2 ) 2 Na 3 P 4 2 3 Zn-2 184 (4) Et 2 2 2 2 5 5 N r 3 Na 2 2 2 R 2 3 3 2 2 () 2 (5) Et S 2 Et Mg Et 2 EtMg Me 3 KMn 4 Mg EtMe 2 Et Me Et()Me Et () () Me Al 2 3 2

Wittig Et()Me 2 S 4 KMn Me Me 4 K Me Me KMn 4 EtMg MeMe 7. (1) A: B: () 3 Et Me Et () () Me : D: () E: 2 KMn 4 2 D α - Me Me () ()E (2) A: B: Me Me : D: ( 2 ) 3 Me A ()B D 3 2 (3) A( ) 2 2 5 B 2 A 3-3- 3-2,3-3,4- () 3 2,3-3,4- (4) A: Et B: Et () : I D: Et A 5 B () 2 5 A 185

1. 2 2. (1) R 1 4 3 2 1 R 2 3 4 α- (2) (3) (4) 3. (1) R 2 R 2 R 2 S 2 (P 5 ) P 2 5 2 R' 2 R' 2 N 2 LiAl 4 R (R)2 R 2 R' RNR' 2 R2 199

(2) R 2 2 (R) 2 R 2 R R' R2 R' R' 2 N 2 RNR' 2 (3) LiAl 4 R2 (R) 2 2 R' R' 2 N R 2 R 2 R' R 2 RNR' 2 R 2 (4) 2 R 2 R' R 2 R' R'' R'' 2 N LiAl 4 R 2 R'' R' RNR'' 2 R' R2 R' 4. β- R 2 2 R' R'Na R R' 2 2 R' R 2 2 R' R R () () β- β- α- 2 ( 2 R) 2 RNa R'X R' ( 2 R) 2 αβ- 2, X R 2 (X) R 2 2 (X) 5. (1) ( X ) 200

KMn 4 ()2 2 2 R() 2 R2 2 ( 2 ) 2 2 ( 2 2 ) 2 2 2 2 ( 2 2 ) 2 2 2 (2) α- 2R() R R β- αβ- R() 2 2 R 2 γδ- R() 2 2 (3) αβ- R()( 2 ) 3 2 2 2 R R 2 2 [ 1] 201

(1) (2) (3) (4) 2 2 (5) (7) Me Me (6) 2 (8) 2 5 (9) 2 Me (10) N 2 Et (11) (12) -1,2- (1) 4--2-2--4- (2) (3) (4) (5) (6) Z-2--2- (7) ( α-) (8) α--δ-(- 2 5 ) (9) (10) (11) 3 (12) [ 2] (1) P 5 (2) P 2 5 (3) 2 (4) (5) LiAl 4 (6) 2 (7) (8) (9) α- (10) 2- (11) (12) (1) 2 P 5 P 3 (2) (3) 2 5 2 2 2 P 2 5 2 P 2 ( 2 5 ) 2 2 202

(4) 2 2 (5) 2 2 LiAl 4 2 2 (6) 2 2 (7) 2 (8) ( ) 2 () 2 3 2 ( ) 2 (9) (10) 2 2 N 2 (11) 2 5 N 2 5 2 5 (12) 2 5 [3] (1) (2) (3) (4) (5) (1) >> 3 2 > 2 2 >> > 2 5 2 3 (2) - R R 2 R R ( R 2 ) R R R 2 N 2 N >( ) 2 > 2 5 > N 2 (3) αβ-αβ- >> (4) 203

>> (5) 204 ()>( ) 2 ()> () [4] (1) a, 2 4 a 3 Na (2) g 2 g/ 2 R 2 R (3) 2 2 (4) 2 R () 2 R 2 α- (5) β- R 2 2 R 2 α- (6) (7) α- ( 2 2 2 ) 2 2 2 2 ( 2 2 2 ) 2 2 2 R (N 2 ) R 2 N 2 2 [5] 2 /NiLiAl 4 NaB 4 (1) 2 /Ni 2 2/Ni 2

2 /Ni 2 2 2 2/Ni N 2/Ni 2 () () 2 2 2 N 2 2 N 2 /Ni 2 2 N 2 R R (2) NaB 4 X 2/Ni 2 R NaB 4 2 N NaB 4 2 2 R ()N (3) LiAl 4 LiAl 4 R X R LiAl 4 2 2 2 () 2 2 2 2 LiAl 4 2 2 2 5 LiAl 4 2 N 2 2 N 2 LiNa Na/N 3(l) 3 3 2, N 3 3 Li, Na R RR' Na R' Na R 2 R 2 R 2 R' [ 6] (1) (2) (3) (4) (5) (6) (7) (1) KMn 4 KMn 4 24-205

(2) Fe 3 (3) p (4) (5) 3-2,4- (6) KMn 4 2 2 (7) AgN 3 /Et Ag N 3 p [ 7] (1) (2) 2 P 3 (3) ( ) 2 N (4) R (5) 2 5 (6) (7) (8) (9) ( 2 ) 3 2 (10) 2 2 () 2 2 Na S 2 (11) MeMg 2 (12) EtEt Et Na (13) 2 N 2 Et Na (14) 3 2 2 2 5 β-γδ- 206

(1) (2) (3) R 2 2 N( ) 2 (4) 2 (5) (6) 2 5 2 (7) (8) 2 2 (9) (10) 2 (11) 2 Mg 4 (12) 2 5 2 2 5 (13) N (14) 2 5 Na [ 8] (1) Ka 1,2-1,2-2 (2) (3) (R 3 ) (4) (1) 2 2 Ka 2 2 2 Ka 2 (2) -- (3) (R ) (R ) (4) [ 9] (1) 2 2 (2) α- 207

(3) (4) (5) (6) 2--2- (7) 2-- (8) (9) (1) 2 S 4 2 g 2 3 KN N 2 2 3 2 2 2 Mg TF 2 Mg 2 3 2 2 5 5 N r 3 2 2 Ag / N3 2 2 Mg 3 2 2 (2) 2- N 2 2 2S 4 2 ( ) 2 KN ( ) 2 N 3 ( ) 2 2/P K Et 2 ( ) 2 2 3 () KMn 4 3 KN () 3 () N Me (3) 2 2 P/ 2 S 2 2 K Et K Et 2 2 2 2 (4) 2 2 2 2-2 2 208

Mg Et 2 Mg 2 2 2 5 5 N r 3 2 Ag(N 3) 2 2 (5) 1-2-- 3 Na 2 5 2 n-3 7 n- 3 7 2S 4 2 3 2 () KMn 4 3 (6) 2 9-(5) LiAl 4 I 2 /K LiAl 4 3 2 2 5 S 2 2 5 Mg Et 2 2 5 Mg 3 2 5 NaB 4 3 2 S 4 3 () 3 2 3 NaB 4 2 5 2 5 Mg Zn-2 (7) 2- u 2 / 2 Na 2 Ag /N 2 2 3 Pd 2 2 S 2 2 /Ni 2 S 4 2 2 2 2 2 3 2 () 2 2 2 S 4 (8) 2 5 2 S 4 2 2 2 2 2 KN N 2 2 N 209

3 ( 2 2 ) 2 2 5 5 5 N r 3 2 3 S 2 Na 2 Na NaB 4 KMn ( 2 ) 4 2 ( 2 2 ) 2 (9) 9-(8) 2 2 2 2 LiAl 4 2 /Ni 2 () 2 2 2 2 2 KN 3 N( 2 ) 4 N ( 2 2 2 ) 2 3- [10] (1) KMn 4 R 2 R 2 (2) KMn 4 R R 2 (3) S 2 KMn 4 2 (4) 2 2 (5) 2 (6) 3 2 2 R N 2 3 R 3 R N R 2 R 2 R Na 3R R RMg 2 3 2 2 R 2 KMn 4 ( 2 2 2 ) 2 210

( ) 2 KMn 4 R I 2/Na R 2 I 3 [ 11] (1) 3- (2) 1- (3) 1- (4) (5) 2- (6) 5- (1) () KMn 4 2 /Ni r.t. (2) 2 2 /Ni r.t. 2 2 2 2 2 2 2 2 5 Na 2 Ag /N 3 2 2 2 2 2 2 2 () 2 2 2 5 (3) 2 2 2 Mg 3 2 2 2 2 2 2 2 2 5 KMn 4 2 2 2 5 2 2 2 2 2 2 2 KN 3 2 2 2 2 2 2 N 2 5 2 2 2 (4) 2,3- NBS 1- NaB 4 2 5 () 2 2 S 4 5 NBS 2 2 /Ni r.t. 2 2 Mg 3 2 2 2 2 2 2 I (5) 2 /Na ( 2 ) 3 2 5 2 2 2 (6) ( 2 ) 3 ()( 2 ) 4 2 S 4 3 3 7 5 11 KMn 4 2 4 9 4 9 5 11 2 4 9 2 3 7 2 [12] 120ml 2 S 4 120ml 120g (1.62mol) 0.46mol Na 2 r 2 7 20 35 NaS 3 Na 163 ~ 167 (1) (2) (3) NaS 3 2 S 4Na (4) 80~90 ( ) 211

() NaS 3 () Na (1) (2) K 2 r 2 7 2 S 4 n- 4 9 3 7 4 9 n- n- n- 3 7 () 4 9 K 2 r 2 7 n- 2 S 3 7 2 4 9 4 (3) NaS 3 2 S 4 Na 2 S 4 4 9 2 5 2 n- 4 9 2 S 4 (4 9 ) 2 (4) 80~90 [13] (1) (2) 2,4- (1) Na 3 a 2 Na NaS 3 Na 2 3 a 2 Na (2) Fe 3 Fe 3 p - p Fe 3 2 2 2 2 5 2 2 5 [14] (1) n- 5 11 2 n- 10 22 (2) ( ) 2 212

(3) 2 5 2 2 (4) 2 2 (5) n- 3 7 n- 3 7 (6) ( ) 2 2 5 (7) ( ) 3 (Me) 3 2 (8) 2 2 2 2 (1) 1- g n- 5 11 2 n- 5 11 n- 10 22 2, 4 9 2 2/P n- n- 4 9 Na 4 9 () KMn 4 n- n- 4 9 n- 4 9 Mg n- 4 9 4 9 -n n- 10 22 (2) I 2 /K 3 P 2 5 (3 ) 2 K Et 2 /Ni Na 2 /Ni () 2 S 4 3 2 KMn 4 3 P 2 5 (3) 2 2 LiAl 4 3 7 2S 4 n- 2 R 3 (4) Na Ag N 3 3 2 213

KMn 4 3 EtNa 2 2 2 5 2 2 5 NaB 4 3 () 2 2 2 5 3 () 2 β- (5) Et EtNa n- 3 7 2 2 n- S 3 7 2 2 5 n- 3 7 2 2 5 4 NaB 4 n- 3 7 () 2 2 5 2 5 2 5 2 S 4 n- 3 7 2 2 5 LiAl 4 n- 3 7 2 2 5 2 5 2 5 N r 3 n- 3 7 2 5 (6) α- 2 S 4 KMn 4 (2 2 ) 2 2 /P (7) 2- ( ) 3 2 hν ( 2 ) 2 ( ) 3 Mg K/Et ( 2 ) 2 Et 2 () 3 Mg ( ) 3 2 3 2-9 (8) 2 2 2 ( ) 2 ( ) 2 2 ( ) 2 (g) Mg 2 ( ) 2 2 Mg Et 2 3 2 2 [15] 214

(1) 72 KMn 4 142 (2) 1.76g 30mL1.0mol/dm 3 Na 1 0.25mol/dm 3 40mL LiAl 4 (3) 4 6 2 Na Na (4) A 5 4 3 KMn 4 A B B S 2 D A~D (5) A 3mol 2 BB B KMn 4 DD NaS 3 D 1mol E( 6 10 4 ) D 2 FF D 14E (1) 2 144 5~6 142 72 72 2 45 72 45=27 2 3 2 3 2 29 2 2 (2) M R 2 R Na R 2 Na R M 1 1.76 (30 1.0 40 0.25) 10 3 1.76 M = 2.0 10 = 2 88 88 32=56 4 8 4 8 2 LiAl 4 () (3) Na Na 4 6 2 (4) KMn 4 S 2 KMn 4 A A D 215

3 3 A.. 3 B. D. 3 (5) E E D E D F E D F B A 3mol 2 [16] 2 (1) 3 S 3 Na (2) 2 2 2 N (3) 2 2 LiAl 4 (4) 2 2 2 S 4 (5) Na 2 (6) Al 3 (7) 2 ( 2 ) 2 Na I (8) 2 2 Na 2 (9) () 2 2 Na LiAl (10) 4 3 (1) 2 S 3 Na 3 2 (2) 2 2 2 N 216

2 N (3) 2 2 LiAl 4 2 (4) 2 2 2 S 4 2 (5) Na 2 2 (6) Al 3 2 (7) (8) Na 2 ( 2 ) 2 ( 2 ) 2 I Na 2 2 2 2 (9) () 2 2 Na 2 Na LiAl (10) 4 3 2 5 [17] Mg [18] [19] 700 2 700 700 2 2 2 217

2 G 2 (1) 2 (2) N 3 (3) 2 (4) 2 5 (5) (1) (2) (3) (4) (5) 2 2 2 2 2 2 2 N 3 3 N 2 2 ( ) 2 2 5 [ 20] (1) (2) 2 2 5 2 > 2 > I 2 2 > 2 N 2 > 2 G (3) N 2 2 N F 2 < 2 < 2 (4) 2 > F 2 > 2 F F (5) 2-1- K a 6- K a (1) >>I >> (2) >>>> (3) F>> (4) F 2 >> (5) 1--2- K a 6- K a [ 21] Na (1) 2 2 Na (2) 2 2 218

Na (3) ( 2 ) 4 (4) () 2 2 2 () 2 Na (5) (R) ( ) 2 5 (6) (R) (7) 2 ( )( 2 5 ) 3 7 -n (8) Na 2 (1) Na 2 2 Na (2) 2 2 2 2 EtNa (Et) 2 2 Et Na Na [ ] 2 2 2 2 2 2 2 2 Na (3) δ- ( 2 ) 4 2 Na (4) ( 2 ) 2 2 2 ( 2 ) 2 2 2 2 2 2 2 (5) Na (R) 2 2 5 2 3 2 (R) 3 2 5 (6) (R) 2 3 7 -n 2 5 Na 2 n 2 2 5 (R) 3 7 -n 2 5 (S) 3 7 -n (7) β γ-β-γ- 2 2 2 2 2 (8) 219

( 2 Et) 2 EtNa 2 Et Et 2 2 2 Et [22] (1) ( 6 5 2 ) 2 2 (2) ( ) 2 2 2 5 (3) Et 3 2 (4) 2 5 (5) (6) 2 5 α- α- (1) α- 2 2 2 5 2 5 Na 6 5 2 2 2 5 2 6 5 2 5 Na 6 5 2 2 2 5 ( 2 6 5 ) 2 Na ( 6 5 2 ) 2 2 2 ( 2 2 5 ) 2 3 2 5 Na 6 5 2 ( 6 5 2 ) 2 2 2 5 Na 6 5 2 ( 6 5 2 ) 2 ( 2 2 5 ) 2 (2) (1) (3) α- (4) α- α- α- α- α- 2 ( 2 2 5 ) 2 2 5 Na 2 5 2 5 ( 2 2 5 ) 2 EtNa Et 2 Et 2 5 ( 2 2 5 ) 2 2 5 2 2 5 Na 2 3 2 5 2 2 5 2 2 2 5 2 5 ( 2 5 ) 2 2 5 Na 3 2 5 2 2 2 5 2 2 5 2 5 2 (5) 1,3-220

2 5 Na 2 2 2 5 2 2 5 2 ( 2 ) 2 2 2 2 2 5 Na Na 3 2 2 5 (6) 2- α- 2 ( 2 2 5 ) 2 2 5 Na ( 2 ) 3 ( 2 2 5 ) 2 ( 2 ) 3 2 5 Na 2 2 5 3 2 2 S 2 Et 2 2 5 EtNa Et 5 2 2 2 5 Na 2 5 1--2- [ 23] (1) A 7 14 3 B DB B EE D ABDE (2) A( 5 10 2 )/ B( 8 14 3 )B B / ( 10 18 2 ) D( 7 14 )D D - 3- A~D (3) A( 8 14 4 ) 2,4- A B( 7 12 )B 2,4- B ( 7 12 4 ) D( 7 10 3 )A LiAl 4 E( 8 18 2 )E 3,4--1,5- A~E (1) A 2 B B (DE ) E D E DA D D D 2-D E 3-B β- A 3- A: 2 2 ( ) 2 B: 2 2 : D: E: 2 2 (2) AB AB /B A α- 221

α- D D 3- A 2 B ( ) 2 5 2 2 5 2 5 ( ) 2 5 2 2 5 D 2 5 ( ) 2 5 2 2 5 (3) A A BB B DD D A A 2 2 ( )( ) 2 2 E 2 2 2 2 Me Me A 2 2 Me 2 Me D Me ( )( ) Me B 2 1. (1) 2/P (2) S 2 (3) Mg (4) N 2 (5) LiAl 4 (6) (7) / 2. (1) 2 LiAl 4 (2) 2 2 5 NaB 4 (3) 2 (4) 2 /Ni 2 r.t. 222

2 ( 2 ) 2 2 Na (5) (6) Na 3. (1) 2 2 2, 2 5 2 (2) (3) (4) 2,4-1,3- (5) AgN 3 /1- (6) 2,2- (7) 4. (1) (2) (3) α- (4) (5) (6) 2--3-5. (1) (2) LiAl 4 (3) (4) (5) (6) 1,8- (7) 2,2'- 6. (1) 2--4-2-3--2- (2) 7. (1) AB 5 8 2 Na AB A B KMn 4 AB (2) A 3 6 2 Na 3 A BB 5 8 3B B 7 12 3 Na D D 5 10 D NaS 3 A~D (3) AB 4 6 4AB Na 3 A 4 4 3B 3 6 2 D ED E KMn 4 223

AB 2 /P 1.(1) ( ) 2 2 ( ) 2 2 (2) (3 ) 2 2 S 2 ( ) 2 (3) ( ) 2 2 Mg ( ) 2 2 Mg 4 N 2 (4) (3 ) 2 2 ( ) 2 N LiAl (5) 4 (3 ) 2 2 ( ) 2 2 ( (6) 3 ) 2 ( ) 2 2 [( ) 2 ] 2 2 (7) ( ) 2 2 ( ) 2 2. (1) 2 LiAl 4 2 (2) NaB 4 2 2 5 () 2 2 5 (3) 2 2 2 224 2 /Ni (4) 2 r.t. 2 2 2 (5) ( 2 ) 2 2 2 2 (6) 2 Na 2 Na 2 3. (1) spsp 2 sp 3 S σ() 2 > 2 2 > 2 5 2 (2) >> (3) >> (4) 2,4-1,3-2,4-> >1,3- (5) AgN 3 >>1-

(6) 2 2 5 > 2 2 2 5 >( ) 3 2 2 5 (7) >> 4. (1) Fe 3 (2) KMn 4 KMn 4 2,4- (3) α- KMn 4 2,4-α-()( ) (4) AgN 3 / (5) (Fe 3 2 )() (6) 2--3-3- ( Fe 3 ) 5. (1) NN (2) ( 2 ) 4 Et (3) 2 5 Et (4) Et 2 2 2 Et (5) (6) (7) 2 2 5 6. (1) 2 ( ) 2 α-α- ( ) 2 α- 2 5 Na 2 2 2 5 2 2 5 Na 3 2 2 2 Na 3 2 2 2 Na 225

2-2- EtNa 2 2 2 5 2 2 5 Na 2 Et 2 NaB 4 Et 2 () Et 2 Et 2 ( ) 2 2 αβ-α- EtNa 2 2 2 5 2 2 5 Na 2 2 2 /P 2 K/Et 2 ( ) 2 2 (2) 1,4-2 1,4-1,4-3- NBS Se 2 α- 2 KN 2 1 mol 2 2 2 3 N 2 2 N ( 2 2 2 ) 2 2 /Ni P 2 5 N 3 2 ( 2 2 ) 2 2 2 2 Na 5 5 N r 3 Ag /N 3 KN N 2 2 2 2 3 2 /Ni NBS 2 2 ( 2 2 ) 2 2 2- NBS NBS 2 3 g 2 2 Na Ag /N 2 2 3 Na 5 5N r 3 Ag /N 3 Se 2 226

7. (1) AB AB A B ( 2 ) () γ- A 2 2 2 B 2 2 2 5 (2) A A 4 A B α- 2 (A) MeNa MeI MeNa 2 2 (B) ( ) 2 3 ( ) 2 MeNa MeI ( ) 2 2 () (3) AB AB A B KMn 4 2 A 2 2 2 2 B ( 2 ) 2 ( 2 ) 2 227

1. (1) R N R N N N N (2) α- N 2 N Na 1 2 1 2 2 N Na (3) p FeZnSn N 2 Fe N 2 2 N-() N 2 Zn N4/2 N 242

N 2 Na N N N 2 2 Fe Na N N Fe Zn Na N N N 2 N 2 N 4 S N 2 N 2 N 2 Sn 2 N 2 N 2 N 2 N 2 N 4 S N 2 N 2 Sn 2 N 2 2 N N 2 Na 2 S 2 N N 2 2 N 2 N 2 u NiPt (4) Friedel-rafts Na/ 2 200 N 2 Na 2 3 / 2 130 N 2 243

N 2 Na 2 3 / 2 100 N 2 2 N N 2 2 N N 2 Na 2 3 / 2 N 2 N 2 () 2. (1) N 3 (1 ) (2 ) (3 ) () (2) () a. b. RN2 R' ArS 2 RN 2 RX N 2 R 2 N RX R 3 N RX R 4 N X R'NR ArS 2 NR () N 2 R2 N R' ArS 2 R'NR 2 ArS 2 NR () 244

R 3 N R' ArS 2 c. N NaN 2, X RN 2 R N 2 ArN 2 NaN 2, X 0~5 ArN N R 2 N NaN, X 2 R 2 N N () R 3 N NaN, X 2 (3) N 2 2 N 2 N 2 I 2 N 2 2 Na 3 I N( ) 2 N 2 N( ) 2 N N () N 2 Na N N N( ) 2 (4) N 2 N 3 N 2 N N N 2 N 2 N 2 245

N 2 N N N 2 2 N 2 N 3 S 4 2 S 4 180~200 (5) 2 N ArN 2 ArN 2 () () [] S 3 RX N 3 RN 2 RN 2 RX RX RX R2 N R 3 N R 4 N X R R' N 3 2, Ni R"N 2 2, Ni R N 2 1 R' R NR" 2 R' R 2 N 2 N 3 2 2 R N R 2 N Ni 2 ofmann RN 2 2 RN 2 Na Gabriel 246

N 3 N K RX NR - RN 2 Gabriel 3. (1) N 2 N( N) N N 2 2 N 2 N 2 2 5 RN N X (X N S 3 Na ) X ( X ) 6 5 N N N N N 6 5 N N S 3 Na() Ar N 2 X ( Ar N NX ) 6 5 N 2 () 6 5 N 2 S 4 N N 6 5 N N 6 5 N N 1,2-2 N N N 2,4--4 - ( ) 2 N N N S 3 Na 4 --4- N N 1--2- (2) N 2 NaN 2 0~5 N 2 Na 2 (3) N 2 () 247

() ArN 2 u ArN 2 S 4 KI Ar N 2 ArN 2 u ArI N 2 Ar N 2 un ArN 2 S 4 ArN N2 KN BF ArN 2 S 4 4 ArN 2 BF 4 ArF N2 BF 3 ArN 2 S 4 2 Ar N 2 NaN 2 u ArN 2 N 2 ArN 2 S 3 P 2 4 Ar N2 ArN 2 Sn 2 ArNN2 N 2 N N N 2 N( ) 2 N N N( ) 2 Na (Ar N N Ar N N ) () (Ar N N Na ) [ 1] ( N 2 ) (0.121nm) N N 8 10 5 248

R N N N p-π( π ) 4 3 N N N N [ 2] ( 10g/100g 2 ) (µ = 3.4D) - [3] 2-2->> 3 3 N N N 3 [ 4] 2,4- Na 2,4-1 2 1 2 2 2 2 2 S N 1 S N 2 2 2 2,4- S N 2 249

2 N N 2 2 N δ δ N 2 N 2 2 N 2,4- p-π () [ 5] (1) N 2 2 N 2 N 3 6 5 N 2 N 2 N 2 N 2 N 2 (2) a. b. c. d. N 2 N 2 (1) 2 N 2 >N 3 > 6 5 N 2 > N 2 I ( ) (2) a>b>d>c a cd c d d c [ 6] a. b. c. d. b>a>c>d p-π N N [ 7] 250

(1) a. 2 N 2 b. ( ) 3 N 2 c. o- 6 4 (N 2 ) (2) a. N 2 b. N 2 c. N( ) 2 d. N( ) 2 (3) a. N 2 b. N ( ) 2 c. 2 N 2 N 2 (4) a. N b. N c. (5) a. N 2 b. 2 N 2 c. 2 N N 2 N 2 (6) a. b. N 2 c. d. (1) a α- b α-c α- (a ) a b c a Na Fe 3 2 c (2) ab cd ac bd a a 2 b S 2 b 2 c Na 2 c NaN 2 d d 251

a b c d NaN 2 <5 N 2 N 2 (3) a b c a () b a a Na b c AgN 3 b 2 (4) ac b c α- a a I 2 b c c (5) a b c a b AgN 3 c a c 2 2 (6) a bd ab a a a Fe 3 b 2 b c 2 c d d c NaN 2 N 2 d N 2 [ 8] (1) (2) N, N- (1) 252

Na (2) () N, N- NaS 3 N, N- 3 [ 9] (1) 3 2 (2) N( ) 2 N (3) N (4) ( ) 3 N 2 6 5 (5) 2 N( 2 ) 3 N 2 (6) 2 2 N 2 (7) N 2 (8) (3 ) 3 N 2 (1) () 2-() N, N- -2- (2) N,3-() (3) 4,4 - (4) (5) 4-γ- (6) 2-(2-) (7) 1,4- (8) (1-) [ 10] (1) (2) 1,3- (3) β- (4) 253

(5) -NN- (6) (7) N- (8) α- (1) ( ) 2 2 N 2 (2) 2 N 2 2 (N 2 ) 2 (3) ( ) 2 N 2 2 (4) 6 5 N 3 (5) 2 N N( ) 2 (6) ( 2 5 ) 4 N (7) 2 N N 2 (8) N N 2 [ 11] (1) (2) (3) 3,5-3,5- (4) 1,4- (5) (6) α- (1) 2 N 3 ( (N 2 ) 2 u 2 3 P 3 () 4 N 3 () (N 2 ) (2) 2 2 2 Zn 2 2 2 2 NaN 2 2 2 N 2 3 2 2 2 2 N 2 Pt ofmann N 3 2 2 2 KMn 4 2 2 N 3 2 2 N 2 2 2 2 N 2 (3) ofmann (2) 254

N 3 () P 3 N 3 N 2 2 N 2 (4) 2 2NaN 2 2 2 2 N 2 2 N 2 Pt 2 N 2 2 2 2 N 2 (5) (1) 2 ( ) 2 S 2 2 S 2 N 3 ( ) 2 () 2 N 2 2 ( ) 2 N 2 2 5 N( ) 2 S 2 N3 u 2 2 2 N 2 ( ) 2 ( ) 2 2 N 2 2 ( ) 2 Ni 2 5 N( ) 2 (6) 3 ( X ) 2 S 2 N 3 2 2 N 2 KMn 4 P 3 2 Al 6 3 6 6 5 6 5 2 N 2 3 2 Ni [ 12] 6 5 ( )N 2 5 1mol( ) 2,K 2 3 2 2 N 2 2 N 2 1mol( ) 2, K 2 3 2 2 N 3 255

( ) K 2 3 2 2 N 3 2 2 2 2 N 2 N [13] [14] 25% 13%1-2-37%5%3%(1) (2) (1) N 2 [ 322 2 ] N (2) 2 2 2 N 2 2 2 2 2 N 2 N 2 [ 2 2 2 ] ( ) ( ) 2 2 2 2 2 2 2 2 2 2 ( ) ( ) 2 () 2 2 2 2 [15] 2,4-2,4,6- (1) (2) Ar 256 N N Ar N N () ()

[ 16] β-, NaN 2 N 2, 2 ~(1) (2) (1) ( ) 2 ( ) 2 ( ) 2 ( ) 2 2 ( ) 2 ( ) 2 2 ( ) 3 ( ) 3 ( ) 3 N 2 N 2 N 2 2 2 N 2 2 N 2 () (2) β- N 2 N 2 N 2 Pd NaN 2-2 N 2 N 2 2 [17] A( 4 9 N) A B( 4 11 N)B A ( 7 18 IN) D( 4 6 )D E( 10 12 4 )E ABD 257

E A ( 4 9 N) A A A -A B( 4 11 N) B ofmann B 2 2 2 N 2 A 2 2 2 N 2 DE 2 2 2 N 2 2 2 2 N 2 3 A Zn, 2 2 2 2 N 2 2 B 2, 2 2 2 N 2 2 2 2 N 2 2 2 2 N( ) 3 A 2 2 D l E 2 2 Pd I Ag 2 2 2 [18] A B 6 15 N A 5 13 N B 1-3 9 N A B AB A B A B 2 2 2 N( ) 2 ( ) 2 N( ) 2 [19] 15 15 N AA BB B AB A A B A ( ) B ( B ) A B A B N- A N N Na - N A B 258