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Synlett 1995; 1995(9): 943-944
DOI: 10.1055/s-1995-5129
DOI: 10.1055/s-1995-5129
letter
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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
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
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