CONCOMITANT EPOXIDE DEOXYGENATION AND DEACETYLATION OF GLYCIDYL ACETATES INDUCED BY TELLURIDE ION

Authors
DITTMER DC ZHANG Y DISCORDIA RP
Citation
Dc. Dittmer et al., CONCOMITANT EPOXIDE DEOXYGENATION AND DEACETYLATION OF GLYCIDYL ACETATES INDUCED BY TELLURIDE ION, Journal of organic chemistry, 59(5), 1994, pp. 1004-1010
Citations number
48
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
5
Year of publication
1994
Pages
1004 - 1010
Database
ISI
SICI code
0022-3263(1994)59:5<1004:CEDADO>2.0.ZU;2-B
Abstract
Treatment of glycidyl acetates with telluride ion (Te2-) produced by r eduction of elemental Te with LiEt(3)BH yields allylic alcohols by los s of the epoxide oxygen atom and the acetyl group from the ester. If t he glycidyl acetate is disubstituted at C-3, a rearrangement to an iso meric allylic alcohol competes with the deoxygenation-deacetylation. T riethylborane, a byproduct in the reduction of Te, is believed to play an important role as a Lewis acid since when it is absent or removed by addition of fluoride ion the reaction is extremely slow.