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Thermolysis of dimethyl cis- and trans-1 pthalimidoaziridine-2,3-dicarboxylates in the presence of dipolarophiles


Kuznetsov, M A; Ushkov, A V; Selivanov, S I; Pan'kova, A S; Linden, A (2009). Thermolysis of dimethyl cis- and trans-1 pthalimidoaziridine-2,3-dicarboxylates in the presence of dipolarophiles. Russian Journal of Organic Chemistry, 45(8):1200-1207.

Abstract

Thermolysis of dimethyl esters of stereoisomeric phthalimidoaziridine-2,3-dicarboxylic acids in the presence of dimethyl fumarate, dimethyl maleate, and N-phenylmaleimide occurred stereo-specifically and stereoselectively led to the formation of derivatives of 1-phthalimidopyrrolidine, products of 1,3-dipolar additrion of intermediately arising azomethine ylides. In keeping with the rules of the conservation of orbital symmetry the thermal opening of the 2,3-disubstituted 1-phthalimidoaziridines into azomethine ylides occurred conrotatory. The relative positions of the substituents in the dipolarophiles is retained in the reaction products indicating the concerted addition mechanism.

Thermolysis of dimethyl esters of stereoisomeric phthalimidoaziridine-2,3-dicarboxylic acids in the presence of dimethyl fumarate, dimethyl maleate, and N-phenylmaleimide occurred stereo-specifically and stereoselectively led to the formation of derivatives of 1-phthalimidopyrrolidine, products of 1,3-dipolar additrion of intermediately arising azomethine ylides. In keeping with the rules of the conservation of orbital symmetry the thermal opening of the 2,3-disubstituted 1-phthalimidoaziridines into azomethine ylides occurred conrotatory. The relative positions of the substituents in the dipolarophiles is retained in the reaction products indicating the concerted addition mechanism.

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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:2009
Deposited On:13 Oct 2009 09:24
Last Modified:05 Apr 2016 13:22
Publisher:Springer
ISSN:1070-4280
Additional Information:The original publication is available at www.springerlink.com / Original Russian Text © M.A. Kuznetsov, A.V. Ushkov, S.I. Selivanov, A.S. Pan’kova, A. Linden, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 8, pp. 1209–1216
Publisher DOI:https://doi.org/10.1134/S1070428009080144
Permanent URL: https://doi.org/10.5167/uzh-21135

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