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

✍ Scribed by Christjohannes Jenny; Peter Wipf; Heinz Heimgartner

• Publisher: John Wiley and Sons
• Year: 1986
• Tongue: German
• Weight: 423 KB
• Volume: 69
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19860690809

✦ Synopsis

190, CH-8057 Zurich (22.1X.86)

Carbophilic Additions of Organocuprates and 1,3-Thiazole-5(4H)-thiones

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,S-dihydro-l,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-S(4H)-thione l a with tert-butyl cuprate leads to l a (Scheme 3).