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Thia- and selenaheterocycles by a four-component reaction using elemental sulfur and selenium


Atanassov, P K; Linden, A; Heimgartner, H (2006). Thia- and selenaheterocycles by a four-component reaction using elemental sulfur and selenium. Journal of Sulfur Chemistry, 27(3):181-191.

Abstract

The course of the four-component reactions of (2-benzimidazolyl) acetonitrile, carbondisulfide, isothiocyanate, and sulfur and selenium, respectively, is quite different. Whereas in the case of sulfur a tetracyclic [1,3]thiazolo[4 ,5 :4,5]pyrimido[1,6-a]benzimidazol-2(3H)-thione is formed, a zwitterionic 7-(benzimidazolium-2-yl)-[1,2]thiaselenolo[2,3-b][1,2,4]thiaselenazole-6-thiolate (an azaselenadithiapentalene) is the product in the case of selenium. The structures of the products have been established by X-ray crystallography, and reaction mechanisms for their formation are proposed.

The course of the four-component reactions of (2-benzimidazolyl) acetonitrile, carbondisulfide, isothiocyanate, and sulfur and selenium, respectively, is quite different. Whereas in the case of sulfur a tetracyclic [1,3]thiazolo[4 ,5 :4,5]pyrimido[1,6-a]benzimidazol-2(3H)-thione is formed, a zwitterionic 7-(benzimidazolium-2-yl)-[1,2]thiaselenolo[2,3-b][1,2,4]thiaselenazole-6-thiolate (an azaselenadithiapentalene) is the product in the case of selenium. The structures of the products have been established by X-ray crystallography, and reaction mechanisms for their formation are proposed.

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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 06:45
Last Modified:05 Apr 2016 15:19
Publisher:Taylor & Francis
ISSN:1741-5993
Funders:Swiss National Science Foundation , F. Hoffmann-La Roche AG, Basel
Additional Information:This is an electronic version of an article published in Atanassov, P K; Linden, A; Heimgartner, H (2006). Thia- and selenaheterocycles by a four-component reaction using elemental sulfur and selenium. Journal of Sulfur Chemistry, 27(3):181-191. Journal of Sulfur Chemistry is available online at: www.tandfonline.com with the open URL of your article http://www.tandfonline.com/openurl?genre=article&issn=1741-5993&volume=27&issue=3&spage=181
Publisher DOI:https://doi.org/10.1080/17415990600600097
Permanent URL: https://doi.org/10.5167/uzh-54092

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