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Carbophile Additionen von Organocupraten mit 1,3-Thiazo1-5(4H)-thionen


Jenny, Christjohannes; Wipf, Peter; Heimgartner, Heinz (1986). Carbophile Additionen von Organocupraten mit 1,3-Thiazo1-5(4H)-thionen. Helvetica Chimica Acta, 69(8):1837-1843.

Abstract

Organocuprates and 1,3-thiazole-S(4H)-thiones 1 react in THF at 0° via carbophilic addition onto the C=S bond to give 4,5-dihydro-1,3-thiazole-S-thiols 3 (Scheme 3). This observation is in marked contrast to the previously described reaction of organolithium compounds and 1, which undergo a thiophilic addition onto the exocyclic S-atom. As an exception, treatment of the 1,3-thiazole-5(4H)-thione 1a with tert-butyl cuprate leads to 7a (Scheme 3).

Abstract

Organocuprates and 1,3-thiazole-S(4H)-thiones 1 react in THF at 0° via carbophilic addition onto the C=S bond to give 4,5-dihydro-1,3-thiazole-S-thiols 3 (Scheme 3). This observation is in marked contrast to the previously described reaction of organolithium compounds and 1, which undergo a thiophilic addition onto the exocyclic S-atom. As an exception, treatment of the 1,3-thiazole-5(4H)-thione 1a with tert-butyl cuprate leads to 7a (Scheme 3).

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Additional indexing

Other titles:Carbophilic Additions of Organocuprates and 1,3-Thiazole-5(4H)-thiones
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:03 Jun 2014 07:03
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
Publisher DOI:https://doi.org/10.1002/hlca.19860690809

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