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Chemoselective insertion of dimethoxycarbene into the N-H bond of thiolactams with diverse ring size


Mloston, G; Kania, K; Heimgartner, H (2009). Chemoselective insertion of dimethoxycarbene into the N-H bond of thiolactams with diverse ring size. Journal of Sulfur Chemistry, 30(3-4):278-286.

Abstract

Thermal decomposition of 2,5-dihydro-1,3,4-oxadiazole 4 in toluene solution in the presence of thiolactams 7 or corresponding lactams 11 result in the chemoselective formation of the N-(dimethoxy)methyl derivatives 8 and 12, respectively. The products of both types are formed via insertion of dimethoxycarbene 2a into the N−H bonds. A reaction mechanism via the intermediate ion pair 14/15 or a complex of type 13 is postulated to explain the formation of the products.

Abstract

Thermal decomposition of 2,5-dihydro-1,3,4-oxadiazole 4 in toluene solution in the presence of thiolactams 7 or corresponding lactams 11 result in the chemoselective formation of the N-(dimethoxy)methyl derivatives 8 and 12, respectively. The products of both types are formed via insertion of dimethoxycarbene 2a into the N−H bonds. A reaction mechanism via the intermediate ion pair 14/15 or a complex of type 13 is postulated to explain the formation of the products.

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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:June 2009
Deposited On:25 Nov 2009 12:57
Last Modified:06 Dec 2017 21:45
Publisher:Taylor & Francis
ISSN:1741-5993
Funders:Rector of the University of Lodz
Publisher DOI:https://doi.org/10.1080/17415990902870935

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