Publication: Carbophile Additionen von Organocupraten mit 1,3-Thiazo1-5(4H)-thionen
Carbophile Additionen von Organocupraten mit 1,3-Thiazo1-5(4H)-thionen
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Jenny, C., Wipf, P., & Heimgartner, H. (1986). Carbophile Additionen von Organocupraten mit 1,3-Thiazo1-5(4H)-thionen. Helvetica Chimica Acta, 69(8), 1837–1843. https://doi.org/10.1002/hlca.19860690809
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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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Jenny, C., Wipf, P., & Heimgartner, H. (1986). Carbophile Additionen von Organocupraten mit 1,3-Thiazo1-5(4H)-thionen. Helvetica Chimica Acta, 69(8), 1837–1843. https://doi.org/10.1002/hlca.19860690809