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Reactions of Thioesters with Organic Azides - A Novel Access to Imidates and Thioimidates


Mloston, Grzegorz; Romanski, Jaroslaw; Heimgartner, Heinz (2001). Reactions of Thioesters with Organic Azides - A Novel Access to Imidates and Thioimidates. Polish Journal of Chemistry, 75(7):975-982.

Abstract

The reaction of O-methyl thiocarboxylates 8a, b with organic azides at 110°C yielded the corresponding imidates of type 9, which were easily hydrolyzed to give amides 10. The formation of 9 can be rationalized by a 1,3-dipolar cycloaddition of the azide with the C=S group, followed by the 'two-fold extrusion' of N2 and S. The analogous reaction with methyl dithiobenzoate (11) led to thioimidates 13. On heating, the latter were transformed into thioamides 12.

Abstract

The reaction of O-methyl thiocarboxylates 8a, b with organic azides at 110°C yielded the corresponding imidates of type 9, which were easily hydrolyzed to give amides 10. The formation of 9 can be rationalized by a 1,3-dipolar cycloaddition of the azide with the C=S group, followed by the 'two-fold extrusion' of N2 and S. The analogous reaction with methyl dithiobenzoate (11) led to thioimidates 13. On heating, the latter were transformed into thioamides 12.

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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:2001
Deposited On:23 Oct 2013 06:45
Last Modified:19 Feb 2018 22:06
Publisher:Polskie Towarzystwo Chemiczne
ISSN:0137-5083
Funders:Polish State Committee for Scientific Research (Grant No. 3 TO9A 007 16), Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
OA Status:Closed
Related URLs:http://www.ichf.edu.pl/pjch/pj-2001/pj072001.htm

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