Methylsulfenylation of thioacetals as a method for synthesizing 2-thio-substituted furans

Authors
Padwa, A Ginn, JD McClure, MS
Citation
A. Padwa et al., Methylsulfenylation of thioacetals as a method for synthesizing 2-thio-substituted furans, ORG LETT, 1(10), 1999, pp. 1559-1561
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
10
Year of publication
1999
Pages
1559 - 1561
Database
ISI
SICI code
1523-7060(19991118)1:10<1559:MOTAAM>2.0.ZU;2-5
Abstract
[GRAPHICS] The dimethyl(methylthio)sulfonium tetrafluoroborate induced cyclization of various bis(methylsulfanyl) carbonyl compounds is described. The reaction p roceeds by methylthiolation of the thioacetal group to give a thionium ion which undergoes subsequent cyclization with the neighboring carbonyl group. This is followed by an elimination reaction to furnish the furan ring.