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A Ring-Enlargement Reaction Yielding 1,2,5-Benzothiadiazonin-6-one 1,1-Dioxides


Orahovats, Alexander S; Linden, Anthony; Heimgartner, Heinz (1992). A Ring-Enlargement Reaction Yielding 1,2,5-Benzothiadiazonin-6-one 1,1-Dioxides. Helvetica Chimica Acta, 75:2515-2519.

Abstract

At room temperature or under reflux in MeCN, 3-amino-2H-azirines 2 and 3,4-dihydro-2H-1,2-benzothiazin-3-one 1,1-dioxide (4) give 1,2,5-benzothiadiazonin-6-one 1.1-dioxides 5 in fair-to-good yield (Scheme 2). The structure of this novel type of heterocyclic compounds has been established by X-ray crystallography of 5a (Fig.). A ring expansion via a zwitterionic intermediate of type A' is proposed as the reaction mechanism of the formation of 5.

Abstract

At room temperature or under reflux in MeCN, 3-amino-2H-azirines 2 and 3,4-dihydro-2H-1,2-benzothiazin-3-one 1,1-dioxide (4) give 1,2,5-benzothiadiazonin-6-one 1.1-dioxides 5 in fair-to-good yield (Scheme 2). The structure of this novel type of heterocyclic compounds has been established by X-ray crystallography of 5a (Fig.). A ring expansion via a zwitterionic intermediate of type A' is proposed as the reaction mechanism of the formation of 5.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1992
Deposited On:03 Jan 2014 06:59
Last Modified:08 Dec 2017 01:39
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19920750805

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