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Addition reactions with 1,3-Thiazole-5(4H)-thiones; Synthesis of spirocyclic and fused bicyclic sulfur heterocycles


Heimgartner, Heinz (1991). Addition reactions with 1,3-Thiazole-5(4H)-thiones; Synthesis of spirocyclic and fused bicyclic sulfur heterocycles. Phosphorus, Sulfur and Silicon and the Related Elements, 58(1-4):281-293.

Abstract

Various 1,6-dithiaspiro heterocycles can be synthesized from 1,3-thiazole-5(4H)-thiones via 1,3-dipolar cycloadditions, Diels-Alder reactions, ring expansion of oxiranes, and C-alkenylation followed by radical cyclization. 1,3-Thiazole-5(4H)-thiones with a vinyl substituent at C(4) are photochemically transformed into fused polycyclic compounds or, after C-alkylation to the corresponding 4,5-dihydro-5-mercapto-1,3-thiazoles, into fused bicyclic compounds via radical cyclization. With mCPBA, 1,3-thiazole-5(4H)-thiones are oxidized to thionoxides, which fail to undergo cycloaddition reactions.

Abstract

Various 1,6-dithiaspiro heterocycles can be synthesized from 1,3-thiazole-5(4H)-thiones via 1,3-dipolar cycloadditions, Diels-Alder reactions, ring expansion of oxiranes, and C-alkenylation followed by radical cyclization. 1,3-Thiazole-5(4H)-thiones with a vinyl substituent at C(4) are photochemically transformed into fused polycyclic compounds or, after C-alkylation to the corresponding 4,5-dihydro-5-mercapto-1,3-thiazoles, into fused bicyclic compounds via radical cyclization. With mCPBA, 1,3-thiazole-5(4H)-thiones are oxidized to thionoxides, which fail to undergo cycloaddition reactions.

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Additional indexing

Item Type:Journal Article, refereed, further contribution
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1991
Deposited On:16 Oct 2013 09:08
Last Modified:07 Dec 2017 22:48
Publisher:Taylor & Francis Inc.
ISSN:1042-6507
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1080/10426509108040636

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