Download PDF
Synlett 1999; 1999(9): 1363-1366
DOI: 10.1055/s-1999-32132
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.

Formation of Hydrindans and Tricyclo[4.3.0.03,8]nonanes via 6-Endo Trapping of the Nazarov Oxyallyl Intermediate

C. C. Browder* , F. G. West
  • *Department of Chemistry, University of Utah, 315 S. 1400 East, Rm. Dock, Salt Lake City, UT, 84112-0850
Further Information

Publication History

Publication Date:
31 December 1999 (online)

  PDF Download  Permissions and Reprints All articles of this category

Treatment of trienones 1a-g with BF3 · OEt2 at - 78 °C followed by warming effected Nazarov electrocyclization followed by 6-endo cation-olefin cyclization. The resulting tertiary carbocations underwent elimination to give olefinic products 2, intramolecular hydride transfer to furnish enones 3 and/or 3 + 2 ring-closure providing tricyclic products 4. Use of TiCl4 in place of BF3 · OEt2 led in most cases to a mixture of enones 3 and chloride-trapping products 7.

cyclizations - domino reactions - polycycles - ring closure - tandem reactions