Rearrangements of Penicillin Sulfoxides. 2.1 Spectral Data and X-ray Crystallography of the Novel Imidazo[5,1-c][1,4]thiazine Ring System

Abraham Nudelman, Tali E. Haran, Zippora Shakked

Research output: Contribution to journalArticlepeer-review

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Abstract

The novel imidazo[5,1-c][1,4]thiazine ring system has been obtained by rearrangement of penicillin sulfoxide esters upon treatment with ethoxycarbonyl isocyanate. The unexpected structure of the rearrangement product 4b was established by X-ray analysis. A mechanism involving C5-S cleavage and the formation of an episulfonium ion, D. is postulated.

Original languageEnglish
Pages (from-to)3026-3029
Number of pages4
JournalJournal of Organic Chemistry
Volume46
Issue number15
DOIs
StatePublished - Jul 1981

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