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

doi:10.1055/s-1999-2814

Synlett 1999; 1999(8): 1211-1214
DOI: 10.1055/s-1999-2814

letter

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

PDF Download All articles of this category

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

PDF (90 kb)