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Radical reduction of cyclic xanthates: Formation of alkenes and/or 1,3‐oxathiolanes from 1,3‐oxathiolane‐2‐thiones

Radical reduction of cyclic xanthates: Formation of alkenes and/or 1,3‐oxathiolanes from... AIBN‐initiated radical reactions of 5‐membered cyclic xanthates, 1,3‐oxathiolane‐2‐thiones, with tributyltin hydride are described. Alkenes are formed at 0.025 M concentration of tributyltin hydride, whereas a higher concentration (0.25 M) gives 1,3‐oxathiolanes. A mixture of alkene and 1,3‐oxathiolane is obtained by use of intermediate concentrations. Reactions of cis‐and trans‐4,5‐dialkyl‐1,3‐oxathiolane‐2‐thiones with tributyltin hydride afford E‐alkenes stereoselectively. For an application of this alkene formation reaction, geraniol has been converted to linalool silyl ether in good yield. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

Radical reduction of cyclic xanthates: Formation of alkenes and/or 1,3‐oxathiolanes from 1,3‐oxathiolane‐2‐thiones

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References (12)

Publisher
Wiley
Copyright
Copyright © 1995 Wiley Subscription Services
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.520060409
Publisher site
See Article on Publisher Site

Abstract

AIBN‐initiated radical reactions of 5‐membered cyclic xanthates, 1,3‐oxathiolane‐2‐thiones, with tributyltin hydride are described. Alkenes are formed at 0.025 M concentration of tributyltin hydride, whereas a higher concentration (0.25 M) gives 1,3‐oxathiolanes. A mixture of alkene and 1,3‐oxathiolane is obtained by use of intermediate concentrations. Reactions of cis‐and trans‐4,5‐dialkyl‐1,3‐oxathiolane‐2‐thiones with tributyltin hydride afford E‐alkenes stereoselectively. For an application of this alkene formation reaction, geraniol has been converted to linalool silyl ether in good yield.

Journal

Heteroatom ChemistryWiley

Published: Jan 1, 1995

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