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Synlett 1995; 1995(1): 53-54
DOI: 10.1055/s-1995-4860
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Tandem Radical Cyclisation in the Flash Vacuum Pyrolysis of 2-Methoxyphenyl and 2-Methylthiophenyl Substituted Phosphorus Ylides

R. Alan Aitken* , Charles K. Bradbury, Graham Burns, John J. Morrison
  • *School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK
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Publication Date:
31 December 2000 (online)

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The 2-alkynylphenoxy and -phenylthio radicals, conveniently generated by pyrolytic loss of Ph3PO and Me• from suitably substituted phosphorus ylides, undergo tandem cyclisation leading to tri- and tetracyclic fused benzofurans and benzothiophenes. The fundamental heterocyclic compound benzothieno[3,2-b]benzofuran has been prepared for the first time.

flash vacuum pyrolysis - phosphorus ylides - tandem cyclisation - fused heterocycles - benzothieno[3,2-b]benzofuran