Page 470 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Scheme 5.12. Reductive Removal of Functional Groups from -Substituted Carbonyl 443
Compounds
SECTION 5.6
1 a CH 3 CH 3 Dissolving-Metal
Zn Reductions
(CH CO) O
O 3 2 O
63%
CCH
O 2 3
CH 3
2 b CH 3 Ca O
O
NH 3
80%
3
CH CO 2
3 c O Zn, HCl O
OH CH CO H 75%
3
2
4 d H C OSO CH 3 CH 3
3
2
O Zn O
NH Cl
4
CH 3 CH 3
5 e O O
CH 3 CH 3
O O
Al-Hg
CH
O CH 3 3 O CH 3 CH 3
O OH
6 f O
CH
CH 3 3 O CH Al-Hg CH 3 CH 3 CO 2 H
TBDPSO 3 TBDPSO
CH 3
O O 75%
7 g O O
Al-Hg
O CCH SOCH CH O
CH 3 2 3 3 CCH 3
98%
H
8 h C 5 11 C H
5 11
H H
Zn
N N
H H H
O O CO CH 3 CO 2 CH 3
2
9 i Ph H
O H SmI 2
O
O
CH 3 90%
CH 3
10 j
O O O O
SmI 2
O O 2 CCH 3 O
O O
Ph Ph
(Continued)