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Thiocarbonyl-imide aus der Umsetzung von 2,2,4,4-TetramethyI-3-thioxocyclobutanon mit AryI-aziden


Mloston, Grzegorz; Romanski, Jaroslaw; Linden, Anthony; Heimgartner, Heinz (1993). Thiocarbonyl-imide aus der Umsetzung von 2,2,4,4-TetramethyI-3-thioxocyclobutanon mit AryI-aziden. Helvetica Chimica Acta, 76:2147-2154.

Abstract

Thiocarbonyl Imides from the Reaction of 2,2,4,4-Tetramethyl-3-thioxocylobutanone and Aryl Azides. Reaction of 2,2,4,4-tetramethyl-3-thioxocylobutanone (6) and 4-methoxyphenyl, phenyl, and 4-nitrophenyl azide (7a-c, respectively), at 80°,leads to the 11-aryl-5,10-dithia-11-azadispiro[3.1.3.2]undecane-2,8-diones 8a-c (Scheme 3), respectively, in 67-83% yield. The structure of 8b has been established by X-ray crystallography. The formation of the products may be explained via an intermediate thiocarbonyl imide of type D (Scheme 4), generated by the 1,3-dipolar cycloaddition of the aryl azide with the C=S bond of 6 and elimination of N2.

Thiocarbonyl Imides from the Reaction of 2,2,4,4-Tetramethyl-3-thioxocylobutanone and Aryl Azides. Reaction of 2,2,4,4-tetramethyl-3-thioxocylobutanone (6) and 4-methoxyphenyl, phenyl, and 4-nitrophenyl azide (7a-c, respectively), at 80°,leads to the 11-aryl-5,10-dithia-11-azadispiro[3.1.3.2]undecane-2,8-diones 8a-c (Scheme 3), respectively, in 67-83% yield. The structure of 8b has been established by X-ray crystallography. The formation of the products may be explained via an intermediate thiocarbonyl imide of type D (Scheme 4), generated by the 1,3-dipolar cycloaddition of the aryl azide with the C=S bond of 6 and elimination of N2.

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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:German
Date:1993
Deposited On:26 Dec 2013 09:50
Last Modified:05 Apr 2016 17:19
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche AG, Basel, Polnisches Nationalkomitee zur Förderung der wissenschaftlichen Forschung
Permanent URL: https://doi.org/10.5167/uzh-87452

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