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Additionsreaktion von 1,3-Thiazol-5(4H)-thionen und Inaminen; Bildung von Thioamiden und Thioketonen


Jenny, Christjohannes; Heimgartner, Heinz (1986). Additionsreaktion von 1,3-Thiazol-5(4H)-thionen und Inaminen; Bildung von Thioamiden und Thioketonen. Helvetica Chimica Acta, 69(1):174-183.

Abstract

Ynamines and 1,3-thiazole-5(4H)-thiones of type 1 undergo an addition reaction on heating in toluene yielding mainly alpha,beta-unsaturated 2-(4,5-dihydro-1,3-thiazol-5-yliden)thioamides of type 7 (Scheme 2 and Table). In some cases, 1-diethylamino-1-(4,5-dihydro-1,3-thiazol-5-yliden)-2-alkanethiones 8 have been isolated as minor products. In analogy to other reactions of ynamines with C=O and C=S bonds, a [2+21cycloaddition to thiete intermediates, followed by an electrocyclic ring opening is suggested as reaction mechanism.

Ynamines and 1,3-thiazole-5(4H)-thiones of type 1 undergo an addition reaction on heating in toluene yielding mainly alpha,beta-unsaturated 2-(4,5-dihydro-1,3-thiazol-5-yliden)thioamides of type 7 (Scheme 2 and Table). In some cases, 1-diethylamino-1-(4,5-dihydro-1,3-thiazol-5-yliden)-2-alkanethiones 8 have been isolated as minor products. In analogy to other reactions of ynamines with C=O and C=S bonds, a [2+21cycloaddition to thiete intermediates, followed by an electrocyclic ring opening is suggested as reaction mechanism.

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Additional indexing

Other titles:Addition Reaction of 1,3-Thiazole-5(4H)-thiones and Ynamines; Formation of Thioamides and Thioketones
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1986
Deposited On:04 Jun 2014 08:22
Last Modified:05 Apr 2016 17:54
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche & Co. AG, Basel, Stipendienfonds der Basler Chemischen Industrie zur Unterstützung von Doktoranden auf dem Gebiete der Chemie
Publisher DOI:https://doi.org/10.1002/hlca.19860690121
Permanent URL: https://doi.org/10.5167/uzh-96327

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