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The first reaction of Dimethoxycarbene with an imine moiety


Mloston, G; Heimgartner, H (2007). The first reaction of Dimethoxycarbene with an imine moiety. Helvetica Chimica Acta, 90(9):1758-1764.

Abstract

The nucleophilic dimethoxycarbene (DMC; 2) generated by thermal decomposition of 2,5-dihydro-1,3,4-oxadiazole derivative 1 in boiling toluene reacts smoothly with N-(9H-fluoren-9-ylidene)-4-methylbenzenesulfonamide (7b) to yield carbonimidoate derivative 10. A multi-step reaction pathway, initiated by the attack of DMC onto the C=N bond and followed by the migration of the sulfonyl group (or via a sulfinate anion) is proposed to explain the formation of the final product. In contrast to the formal ketimine 7b, N-benzylidene-4-methylbenzenesulfonamide (7a), a formal aldimine, does not react with DMC under comparable conditions.

Abstract

The nucleophilic dimethoxycarbene (DMC; 2) generated by thermal decomposition of 2,5-dihydro-1,3,4-oxadiazole derivative 1 in boiling toluene reacts smoothly with N-(9H-fluoren-9-ylidene)-4-methylbenzenesulfonamide (7b) to yield carbonimidoate derivative 10. A multi-step reaction pathway, initiated by the attack of DMC onto the C=N bond and followed by the migration of the sulfonyl group (or via a sulfinate anion) is proposed to explain the formation of the final product. In contrast to the formal ketimine 7b, N-benzylidene-4-methylbenzenesulfonamide (7a), a formal aldimine, does not react with DMC under comparable conditions.

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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:2007
Deposited On:07 Nov 2011 13:58
Last Modified:18 Apr 2018 11:41
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Polish Ministry of Science and Higher Education (grant No. PBZ-KBN-126/T09/12), F. Hoffmann-La Roche AG, Basel
OA Status:Green
Publisher DOI:https://doi.org/10.1002/hlca.200790185

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