PDF herunterladen
Synthesis 2000; 2000(10): 1366-1368
DOI: 10.1055/s-2000-7107
short paper
© 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 Cycloocta-3,5-dien-1-ol and Cycloocta-3,5-dien-1-one: SeO2/O2 Oxidation of Dienes

Elena S. Koltun* , Steven R. Kass
  • *Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA; Fax + 1(612)6 26 75 41; E-mail: kass@chem.umn.edu
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

A useful synthesis of cycloocta-3,5-dien-1-ol was developed starting from cycloocta-1,3-diene. Oxidation of the diene with selenium oxide in refluxing acetic anhydride affords the homoallylic and allylic acetates in a 19 : 1 ratio and a 36% overall yield when O2 is bubbled through the reaction mixture. Subsequent reduction with LAH affords the homoallylic alcohol (95%), which can be readily oxidized via TPAP/N-MMO (73%) to the corresponding non-conjugated dienone. This route represents the most efficient method for the preparation of cycloocta-3,5-dien-1-ol and cycloocta-3,5-dien-1-one reported to date, and may provide a general approach to the synthesis of homoallylic alcohols and non-conjugated enones.

selenium oxide - oxygen - homoallylic alcohol - non-conjugated enone - oxidation