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Synlett 1995; 1995(9): 943-944
DOI: 10.1055/s-1995-5129
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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
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Publication Date:
31 December 2000 (online)

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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