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

Authors
Wang, YF Zhang, WH Colandrea, VJ Jimenez, LS
Citation
Yf. Wang et al., Reactivity and rearrangements of dialkyl- and diarylvinylsulfonium salts with indole-2-and pyrrole-2-carboxaldehydes, TETRAHEDRON, 55(35), 1999, pp. 10659-10672
Citations number
10
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
35
Year of publication
1999
Pages
10659 - 10672
Database
ISI
SICI code
0040-4020(19990827)55:35<10659:RARODA>2.0.ZU;2-A
Abstract
Various dialkyl- and diarylvinylsulfonium salts react with indole-2-carboxa ldehydes in the presence of sodium hydride and sodium azide to form tricycl ic azido alcohols analogous to 2. With pyrrole-2-carboxaldehyde, [2,3] sigm atropic and other rearrangements occur except in the case of diphenylvinyls ulfonium trifluoromethanesulfonate where the annulation reaction does take place to give a low yield of 29. (C) 1999 Elsevier Science Ltd. All rights reserved.