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Selenium-containing heterocycles from isoselenocyanates: synthesis of 2-methylidene-1,3-selenazolidine derivatives


Sommen, G L; Linden, A; Heimgartner, H (2006). Selenium-containing heterocycles from isoselenocyanates: synthesis of 2-methylidene-1,3-selenazolidine derivatives. Tetrahedron, 62:3344-3354.

Abstract

A convenient and unequivocal synthesis of the title compounds from isoselenocyanates, malononitrile or 2-cyanoacetate, and 1,2-dibromoethane or a-halogenated carboxylic acid derivatives is reported. The proposed reaction mechanism involves in situ cyclization of different halogenated compounds with an intermediate keten-N,Se-acetal, generated by the base promoted nucleophilic addition of the acidic cyanomethylenes to aliphatic and aromatic isoselenocyanates. Chemical and spectroscopic evidence for the structures of the new compounds is presented.

Abstract

A convenient and unequivocal synthesis of the title compounds from isoselenocyanates, malononitrile or 2-cyanoacetate, and 1,2-dibromoethane or a-halogenated carboxylic acid derivatives is reported. The proposed reaction mechanism involves in situ cyclization of different halogenated compounds with an intermediate keten-N,Se-acetal, generated by the base promoted nucleophilic addition of the acidic cyanomethylenes to aliphatic and aromatic isoselenocyanates. Chemical and spectroscopic evidence for the structures of the new compounds is presented.

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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:2006
Deposited On:22 May 2012 06:58
Last Modified:05 Apr 2016 15:19
Publisher:Elsevier
ISSN:0040-4020
Funders:Dr. Helmut Legerlotz-Foundation, Zürich, f. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1016/j.tet.2006.01.077,

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