Reactivity and rearrangements of dialkyl- and diarylvinylsulfonium salts with indole-2- and pyrrole-2-carboxaldehydes

✍ Scribed by Yufeng Wang; Weihong Zhang; Vincent J Colandrea; Leslie S Jimenez

• Book ID: 104209567
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 742 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00605-5

✦ Synopsis

Various dialkyl-and diarylvinylsulfonium salts react with indole-2carboxaldehydes in the presence of sodium hydride and sodium azide to form tricyclic azido alcohols analogous to 2. With pyrrole-2-carboxaldehyde, [2,3] sigrnatropic and other rearrangements occur except in the case of diphenylvinylsuifonium trifluoromethanesulfonate where the annulation reaction does take place to give a low yield of 29.