PDF herunterladen
Synlett 2001; 2001(12): 1929-1931
DOI: 10.1055/s-2001-18735
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.

The Synthesis of Bridged and Fused Ring Carbocycles Using a Novel Variation of an Intramolecular Nicholas Reaction

Elizabeth Tyrrell* , G. A. Skinner, Tahmina Bashir
  • *School of Chemical and Pharmaceutical Sciences, Kingston University, Penrhyn Road, Kingston KT1 2EE, U. K.; Fax: + 44(020)85477562; E-mail: e.tyrrell@kingston.ac.uk
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
04. Dezember 2001 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

A novel variation of an intramolecular Nicholas reaction is described that provides an efficient method for the synthesis of fused and bridged bicyclic compounds. The mechanism appears to involve an initial regioselective in situ double bond migration of a terminal alkene. The more stable disubstituted alkene then undergoes an intramolecular cyclisation reaction with a dicobalt hexacarbonyl stabilised cation. This transformation generates a second cation, which is subsequently quenched by a halide ion derived from the Lewis acid.

Nicholas reaction - dicobalt hexacarbonyl clusters - fused ring carbocycles - bridged ring carbocycles - double bond migration

      >