DIASTEREOSELECTIVITY IN THE EPOXIDATION OF SUBSTITUTED CYCLOHEXENES BY DIMETHYLDIOXIRANE

Authors
MURRAY RW SINGH M WILLIAMS BL MONCRIEFF HM
Citation
Rw. Murray et al., DIASTEREOSELECTIVITY IN THE EPOXIDATION OF SUBSTITUTED CYCLOHEXENES BY DIMETHYLDIOXIRANE, Journal of organic chemistry, 61(5), 1996, pp. 1830-1841
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
5
Year of publication
1996
Pages
1830 - 1841
Database
ISI
SICI code
0022-3263(1996)61:5<1830:DITEOS>2.0.ZU;2-T
Abstract
Three series of compounds based on the cyclohexene framework. have bee n epoxidized by dimethyldioxirane. A pronounced dependence of epoxide diastereoselectivity on substituent has been observed. In addition the re is a solvent influence on this stereoselectivity. The results have been explained by invoking steric, H-bonding, and dipole-dipole influe nces on the epoxide stereochemistry.