Efficient synthesis of epoxides from vicinal diols via cyclic sulfates

Authors
Jang, DO Joo, YH Cho, DH
Citation
Do. Jang et al., Efficient synthesis of epoxides from vicinal diols via cyclic sulfates, SYN COMMUN, 30(24), 2000, pp. 4489-4494
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
30
Issue
24
Year of publication
2000
Pages
4489 - 4494
Database
ISI
SICI code
0039-7911(2000)30:24<4489:ESOEFV>2.0.ZU;2-N
Abstract
Reaction of cyclic sulfates of vic-diols with sodium hydroxide in THF-MeOH produced the corresponding epoxides in excellent isolated yields at room te mperature. Cyclic sulfates of trans-diols gave cis-epoxides, and cyclic sul fates of cis-diols afforded trans-epoxides exclusively. Various cyclic sulf ates of vic-diols can be converted into the epoxides under the conditions.