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Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes

Crowley, Patrick J and Fawcett, John and Kariuki, Benson M and Moralee, Andrew C and Percy, Jonathan and Salafia, Vittoria (2002) Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes. Organic Letters, 4 (23). pp. 4125-4128. ISSN 1523-7060

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Abstract

Phenylsulfenyl chloride reacts with racemic endo Diels-Alder adduct 4 (DEC ) CONEt2) to afford lactone 8, which can be reduced and protected in a series of high-yielding steps. Key sulfone 10 can be ring opened under strong base conditions to afford vinyl sulfone 11. Attempted desulfonation resulted in the formation of a monofluoroalkene, but a direct desulfonation/eliminative ring opening with strain relief delivered highly functionalized monocyclic species 16.

Item type: Article
ID code: 38951
Keywords: strain relief, monofluoroalkene, ring opening, 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: 04 Apr 2012 14:50
    Last modified: 05 Sep 2014 15:42
    URI: http://strathprints.strath.ac.uk/id/eprint/38951

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