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Synlett 1999; 1999(8): 1211-1214
DOI: 10.1055/s-1999-2814
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Kinetic and Thermodynamic Control in the Synthesis of Tetrahydro-Pyrans and -Furans from 1,4-Diols by Stereospecific Phenylsulfanyl (PhS) Migration: Competition Between exo and endo Transition States and between [1,2] and [1,4]Sulfanyl Participation

Jason Eames* , Nikolai Kuhnert, Francis H. Sansbury, Stuart Warren
  • *University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, England; Fax (0 12 23)33 69 13; E-mail: sw134@cam.ac.uk
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Publication Date:
31 December 1999 (online)

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The factors controlling the cyclisation of 1,4-diols with PhS migration to give THPs rather than THFs are reassessed. Furthermore we provide evidence for a competition between [1,2] and [1,4] sulfanyl participation and cyclisation onto a five membered cyclic sulfonium salt.

cyclisations - heterocycles - thermodynamic and kinetic control - sulfur chemistry - rearrangements