ALKENES FROM CYCLIC SULFATES AND THIONOCARBONATES OF 1,2-DIOLS VIA TELLURIUM CHEMISTRY

Citation
B. Chao et al., ALKENES FROM CYCLIC SULFATES AND THIONOCARBONATES OF 1,2-DIOLS VIA TELLURIUM CHEMISTRY, Tetrahedron letters, 36(40), 1995, pp. 7209-7212
Citations number
49
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404039
Volume
36
Issue
40
Year of publication
1995
Pages
7209 - 7212
Database
ISI
SICI code
0040-4039(1995)36:40<7209:AFCSAT>2.0.ZU;2-B
Abstract
Treatment of 1,2-diol cyclic sulfates (1,3,2-dioxathiolane 2,2-dioxide s) with telluride ion, generated in situ by reduction of the element, yields alkenes rapidly (10 min- 2 h) under mild conditions (0 degrees C to room temperature). The reaction is stereospecific, e.g. meso-2,3- diphenylethane 2,3-diol --> cis-stilbene; d,1-2,3-diphenylethane-2,3-d iol --> trans-stilbene. Unsaturated mannose and ribose derivatives hav e been obtained and diethyl (-)-tartrate gives diethyl fumarate. The r eaction may be performed with 0.1 equiv or less of elemental tellurium in the presence of a stoichiometric amount of reducing agent Reaction of telluride ion with cyclic thionocarbonates (1,3-dioxolane-2-thione s) of meso- and d,l-1,2-dipbenylethane-1,2-diol yields cis- and trans- stilbene, respectively.