Evidence for 1,2-ketocarbenes in thermolysis of sodium o-halogenophenoxides and for benzothiirens in thermolysis of sodium o-bromobenzenethiolates

Authors:
  • JCJ. I. G. Cadogan
    J. I. G. Cadogan
  • JSJohn T. Sharp
    John T. Sharp
  • MTMichael J. Trattles
    Michael J. Trattles
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Abstract
Evidence for the intermediacy of a 1,2-ketocarbene in thermolysis of sodium o-bromophenoxide at 260° in alkyl benzenes to give dibenzo-p-dioxin is provided by trapping reactions with phenols, benzenethiols, and benzamide, benzoxiren being excluded by 13C FT n.m.r. experiments, in contrast to the conversion of sodium o-bromobenzenethiolate into thianthrene, similarly shown to proceed via benzothiiren.