Download PDF
Synlett 1996; 1996(5): 461-464
DOI: 10.1055/s-1996-5446
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Lewis Acid-Catalysed Oxidative Cycloaddition of Thiophenes1

Yuanqiang Li, Michio Matsuda, Thies Thiemann1 , Tsuyoshi Sawada, Shuntaro Matake, Masashi Tashiro2
  • 1Lab. de Química Farmacêutica, Faculdade de Farmácia, Universidade de Coimbra, 3000 Coimbra, Portugal
  • 2Institute of Advanced Material Study, 6-1, Kasuga-koh-en, Kasuga-shi, Fukuoka 816, Japan
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Thiophenes 1 have been treated with m-CPBA under BF3⋅Et2O catalysis. The thiophene-S-monoxides intermediary produced have been reacted in situ with various dienophiles. It could be shown that Lewis acid catalysis enhances the yield of the oxidative cycloaddition of thiophenes considerably. Moreover a greater variety of dienophiles can be used in the corresponding uncatalysed reaction. Thiophene-S-monoxides have also been isolated and subjected to subsequent cycloaddition in a two-step procedure.

cycloaddition - Lewis acid - thiophene-S-monoxide