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

doi:10.1021/jo00328a007

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

Department of Chemistry

Weizmann Institute of Science

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

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 language	English
Pages (from-to)	3026-3029
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	46
Issue number	15
DOIs	https://doi.org/10.1021/jo00328a007
State	Published - Jul 1981

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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.",

author = "Abraham Nudelman and Haran, \{Tali E.\} and Zippora Shakked",

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AU - Haran, Tali E.

AU - Shakked, Zippora

PY - 1981/7

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N2 - 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.

AB - 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.

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

Abstract

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