Page 416 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Scheme 5.4. Reductions with Diimide 389

1 a NaO CN NCO Na SECTION 5.1
2
2
CH 2 CHCH OH CH CH CH OH
2
3
2
2
RCO H, 25°C 78% Addition of Hydrogen at
2
Carbon-Carbon Multiple
Bonds
2 b
C H SO NHNH 2 (CH CH CH S)
(CH 2 CHCH S) 2 7 7 2 3 2 2 2
2
heat 93–100%
3 c NH NH , O ,
2
2
2
Cu(II)
4 d
NH OSO –
O N CH CHCO H 2 3 O N CH CH CO H
2
2
NH OH 2 2 2 2
2
87%
5 e
NH NH 2
2
H O 2
2
46%
6 f O
O O
O KO CN NCO K
2
2
Br Br
87%
7 g O
O CO C H
2
2
CO C H KO CN NCO K 2 2 5
2 2 5
MeOH, HOAc
NO 2
NO 2 95%
O
8 h O
PhS N
PhS N
C H SO NHNH 2
7 7
2
N
N THF,H O, NaOAc
2
ArSO 2
ArSO 2 99%
H O
9 i
N
S
N
H O
hν
(Continued)