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Addition reactions of sulfenyl and sulfinyl chlorides with 3-phenyl-1-azabicyclo[1.1.0]butane


Mloston, G; Woznicka, M; Drabowicz, J; Linden, A; Heimgartner, H (2008). Addition reactions of sulfenyl and sulfinyl chlorides with 3-phenyl-1-azabicyclo[1.1.0]butane. Helvetica Chimica Acta, 91(8):1419-1429.

Abstract

The reactions of 3-phenyl-1-azabicyclo[1.1.0]butane with a-chlorosulfenyl chlorides and sulfinyl chlorides lead to the corresponding sulfenamides and sulfinamides, respectively, which possess an azetidine ring. It is proposed that a two-step mechanism occurs involving an intermediate carbenium ion, which is formed by the addition of the electrophile at the N-atom and cleavage of the N(1) C(3) bond. The structures of 9b and 10b are established by X-ray crystallography.

The reactions of 3-phenyl-1-azabicyclo[1.1.0]butane with a-chlorosulfenyl chlorides and sulfinyl chlorides lead to the corresponding sulfenamides and sulfinamides, respectively, which possess an azetidine ring. It is proposed that a two-step mechanism occurs involving an intermediate carbenium ion, which is formed by the addition of the electrophile at the N-atom and cleavage of the N(1) C(3) bond. The structures of 9b and 10b are established by X-ray crystallography.

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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:August 2008
Deposited On:06 Feb 2009 12:14
Last Modified:05 Apr 2016 12:57
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Rector of the University of Łodz, F. Hoffmann-La Roche AG, Basel
Publisher DOI:10.1002/hlca.200890154
Permanent URL: http://doi.org/10.5167/uzh-12647

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