Rate enhancement in the reduction of (2,3)-α- and (2,3)-β- methylenepenam β-sulfoxides

Robert M. Adlington, Jack E. Baldwin, Gregory L. Challis

Research output: Contribution to journalReview ArticleResearchpeer-review

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The ease of reduction of (2,3)-α-methylenepenam β-sulfoxides, (2,3)- β-methylenepenam β-sulfoxides and bicyclic penam β-sulfoxides to the corresponding sulfides, using potassium iodide and trifluoroacetic anhydride in acetone or N,N-dimethylformamide, was measured. The results indicate that in general the rate of reduction of both (2,3)-α- and (2,3)-β- methylenepenam β-sulfoxides is several orders of magnitude greater than the rate of reduction of bicyclic penam β-sulfoxides. A mechanistic explanation to account for this observation is advanced.

Original languageEnglish
Pages (from-to)8537-8540
Number of pages4
JournalTetrahedron Letters
Issue number46
Publication statusPublished - 12 Nov 1998
Externally publishedYes


  • Penams
  • Reduction
  • Sulfoxides

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