Page 1120 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1096 Scheme 12.11. Synthesis of Epoxides from Alkenes Using Peroxy Acids

CHAPTER 12 A. Oxidation of alkenes with peroxy acids
Oxidations a
1 H
CH CH 2 peroxybenzoic O
acid H
H
69–75%
2 b
peroxybenzoic
acid O
72%
3 c CH
m-chloroperoxy- 3
CH 3
benzoic acid
O
1.1 equiv
CH 3 CH 3 68–78%
4 d HO HO
H H
CH
m-chloroperoxy- 3
O
CH 3 benzoic acid O
O
CH 3 H CH 3 H 87%
5 e CCH CCH
H C O 2 3 H C O 2 3
3
3
m-chloroperoxy-
benzoic acid
OH OH
CH 3 CH 3 CH 3 O 78%
6 f CH 3
CH 3 CH
CONH m-chloroperoxy- 3 O
CH 3 2 benzoic acid CH 3 CONH 2
CH(CH ) CH(CH )
3 2
3 2
B. Epoxidation of electrophilic alkenes 12:1 diastereoselectivity
7 g O O
–
CH 3 H O , OH CH 3 O
2
2
CH CH CH 3
CH 3 3 3 70–72%
8 h
O
Ph C N Triton B Ph C N
+ (CH ) COOH
3 3
H Ph H Ph 76%
9 i O
H CO C H
2 2 5
CH CHCO C H CF CO H
CH 3 2 2 5 3 3
CH 3 H 73%
C. Epoxidation with peroxyimidic Acids
10 j
H O , CH CN O
2
2
3
OH, KHCO
CH 3 3
60%
(Continued)