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

✍ Scribed by Jun'ichi Uenishi; Takayuki Kunugi; Yuki Kubo

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
734 KB
Volume
6
Category
Article
ISSN
1042-7163

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✦ Synopsis

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 1,3-0xathiolane is obtained by use of intermediate concentrations. Reactions of cisand tran~-4,5-dialkyl-I,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 vield.

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