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Synthesis 1989; 1989(1): 42-43
DOI: 10.1055/s-1989-27143
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Desulfonylation of α-Methylthio-α,β-unsaturated Sulfones. A New Route to One Carbon Homologation of Aromatic Aldehydes

Xian Huang* , Han-Zhong Zhang
  • *Department of Chemistry, Hangzhou University, Hangzhou, People's Republic of China
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Publication Date:
27 September 2002 (online)

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α-Methylthio-α,β-unsaturated sulfones 3 prepared from aromatic aldehydes 1 and sulfone 2 react with sodium hydrogen telluride in ethanol to undergo reductive desulfonylation to give vinyl sulfides 4 with certain extent of stereospecificity. A new route to one carbon homologation of aromatic aldehydes 1 to 5 is achieved by hydrolysis of 4 with titanium tetrachloride.

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