Methylsulfenylation of thioacetals as a method for synthesizing 2-thio-substituted furans.
[formula: see text] The dimethyl(methylthio)sulfonium tetrafluoroborate induced cyclization of various bis(methylsulfanyl) carbonyl compounds is described. The reaction proceeds 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.
Padwa
A
A
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Ginn
J D
JD
McClure
M S
MS
D000080:Acetals / Q000737:chemistry*; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry
D000080:Acetals; D005663:Furans