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A novel synthesis of thiophenes from allenic sulfones involving α,β-unsaturated sulfines as intermediates

✍ Scribed by S. Braverman; P.F.T.M. van Asten; J.B. van der Linden; B. Zwanenburg

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
267 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new method for the synthesis of a&unsaturated sulfines by a Peterson alkylidenation of surfur dioxide is described. The required ol-silyl carbaruons are generated by heteroconjugate addrtion of alkyllithium to a-trimethylsilylated allentc suEfones. The ConJugated vinylsuljlnes thus prepared undergo a rapid and unprecedented cycloaromatization to thiophene derivatwes. A mechanism for this remarkable converston 1.7 presented. During the past three decades a large variety of substituted sulfines has been reported'. Thus far, conjugated vinylsulfines received scarce attention in the literature. They have been prepared by oxidation of the

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