PDF herunterladen
Synlett 1993; 1993(1): 27-29
DOI: 10.1055/s-1993-22334
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.

Synthesis of Functionalized 2,5-Dihydrooxepines by [3,3]-Sigmatropic Rearrangement of Cyclopropane Derivatives

Bernhard Hofmann* , Hans-Ulrich Reissig
  • *Institut füur Organische Chemie der Technischen Hochschule Darmstadt, Petersenstrasse 22, W-6100 Darmstadt, Germany
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
19. März 2002 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

Swern oxidation of 2-alkenyl substituted 2-siloxycyclopropyl alcohols provided 2,5-dihydrooxepine derivatives in high yield, while alcohols bearing a 2-styryl substituent gave dihydrofurans. Formation of these heterocycles can be rationalized by ring enlargement of intermediate cyclopropyl aldehydes giving 2,5-dihydrooxepines by [3,3]-sigmatropic rearrange-ment, or dihydrofurans via a stabilized 1,3-zwitterion.

      >