Novel Intramolecular Cyclisations Involving Ketene Radical Intermediates as an Approach to the Synthesis of Polyquinanes

Nicole M. Harrington-Frost; Gerald Pattenden

doi:10.1055/s-1999-2980

Synlett 1999; 1999(12): 1917-1918
DOI: 10.1055/s-1999-2980

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.

Novel Intramolecular Cyclisations Involving Ketene Radical Intermediates as an Approach to the Synthesis of Polyquinanes

Nicole M. Harrington-Frost^* , Gerald Pattenden

^*School of Chemistry, Nottingham University, Nottingham NG7 2RD, England; Fax + 44 115 9 51 35 35; E-mail: gp@nottingham.ac.uk

Abstract

als PDF herunterladen Alle Artikel dieser Rubrik

Treatment of the polyene selenyl ester 1 with Bu₃SnH-AIBN leads to a concise synthesis of the diquinane 6 via a novel cyclisation involving a ketenyl radical intermediate. By contrast under the same radical initiating conditions the selenyl esters 2 and 10 produced cyclopentenone products, viz 9 and 11, and the allene substituted selenyl ester 16 led to the unusual cyclooctadienone 18.

cyclisations - tandem radical reactions

PDF (63 kb)