Reactions of Neopentyl 2,2,2-Trifluoroethanesulfonate (Tresylate) with Nucleophiles: A Model Study for the Coupling of Nucleophiles with Tresyl Agarose

Authors

  • Prof. James F. King,

    Corresponding author
    1. Department of Chemistry University of Western Ontario London, Ontario N6A 5B7 (Canada) Telefax: Int. code + (519)661-3022
    • Department of Chemistry University of Western Ontario London, Ontario N6A 5B7 (Canada) Telefax: Int. code + (519)661-3022
    Search for more papers by this author
  • Manjinder Singh Gill

    1. Department of Chemistry University of Western Ontario London, Ontario N6A 5B7 (Canada) Telefax: Int. code + (519)661-3022
    Search for more papers by this author

  • This work was supported by the Natural Sciences and Engineering Research Council of Canada

Abstract

original image

Not the carbon, nor the sulfur, but rather the hydrogen atom is the site of the attack of a mixture of a basic nucleophile and aqueous NaOH on neopentyl tresylate (1). The elimination–addition sequence is shown below. These observations strongly suggest that the structures assigned to affinity chromatography substrates derived from tresyl agarose should be revised.

Ancillary