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Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction : regiochemical control via the phenylsulfonyl group

Crowley, Patrick J and Fawcett, John and Griffith, Gerry A and Moralee, Andrew C and Percy, Jonathan and Salafia, Vittoria (2005) Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction : regiochemical control via the phenylsulfonyl group. Organic and biomolecular chemistry (18). pp. 3297-3310. ISSN 1477-0520

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    Abstract

    A difluorinated dienophile underwent cycloaddition reactions with a range of furans to afford cycloadducts whichcould be processed regio- and stereoselectively via episulfonium ions, generated by the reaction between their alkenyl groups and phenylsulfenyl chloride. The oxabicyclic products were oxidised to the phenylsulfonyl level and ring opened via E1CB or reductive desulfonative pathways to afford, ultimately, difluorinated cyclohexene or cyclohexane polyols.

    Item type: Article
    ID code: 40325
    Keywords: cyclohexane polyols , Diels–Alder reaction , phenylsulfonyl group, Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry
    Subjects: Science > Chemistry
    Department: Faculty of Science > Pure and Applied Chemistry
    Related URLs:
      Depositing user: Pure Administrator
      Date Deposited: 03 Jul 2012 14:05
      Last modified: 06 Sep 2014 13:53
      URI: http://strathprints.strath.ac.uk/id/eprint/40325

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