Download PDF
Synlett 1995; 1995(9): 943-944
DOI: 10.1055/s-1995-5129
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.

Radical Abstraction vs Cyclisation in Reactions of ortho-Bromophenyl Sulfone Systems: Stereoselective Synthesis of Benz-fused Six and Seven-Membered Ring Sulfones

Christopher D. S. Brown, Allan P. Dishington, Oleg Shishkin, Nigel S. Simpkins*
  • *Department of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, UK, Fax (0115) 951 3564; e-mail Nigel.Simpkins@Nottingham.ac.uk
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

A range of ortho-bromophenyl sulfones undergo radical cyclisation on treatment with Bu3SnH to give benz-fused six or seven membered ring sulfone products. An alternative mode of reaction, involving 1,5-hydrogen atom abstraction, is observed only in two systems, in which radical cyclisation is not possible.

radical cyclisation - radical translocation - cyclic sulfone - enol benzoate