Pummerer rearrangement of thioanhydro-hexitol sulfoxides

J. Kuszmann, P. Sohár, Gy Horváth

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10 Citations (Scopus)

Abstract

Pummerer rearrangement of the 2,5-di-O-acetyl-1,4:3,6-bis(thioanhydro)-D-iditol-disulfoxide (1) isomers gave besides 2-acetyl-thieno-[3.2-b]thiophene (9), 2-acetyl-5-acetoxy-thieno[3.2-b]thiophene (3) as main product. These compounds can be formed only by addition of acetic anhydride to an ylide interintermediate, a fact which enables a more detailed description of the reaction mechanism. Sodium periodate and iodate display a catalytic effect on the rearrangement, yielding a mixture of 2-acetoxy- (6) and 3-acetoxy-thieno[3.2-b]thiophene (7). which are the expected decomposition products of the normal Pummerer reaction. Ferric chloride seems to catalyse an oxido-reduction process, leading mainly to 2-acetyl-thieno-|3,2-b|thiophene.

Original languageEnglish
Pages (from-to)5055-5061
Number of pages7
JournalTetrahedron
Volume27
Issue number20
DOIs
Publication statusPublished - 1971

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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