Permanent URL to this publication: http://dx.doi.org/10.5167/uzh-21135
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.
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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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|Item Type:||Journal Article, refereed, original work|
|Communities & Collections:||07 Faculty of Science > Department of Chemistry|
|Dewey Decimal Classification:||540 Chemistry|
|Deposited On:||13 Oct 2009 09:24|
|Last Modified:||05 Jun 2014 13:08|
|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|
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