The Absolute Configuration of Sulfoxides and Sulfinates

Michael Axelrod, Paul Bickart, John Jacobus, Mark M. Green, Kurt Mislow

Research output: Contribution to journalArticle

Abstract

The absolute configurations of (-)-menthyl (-)-(S)-p-iodobenzenesulfinate and (-)-(R)-3-methylsulfinylpropylamine have been linked by a synthetic sequence involving an odd number of Grignard displacement reactions; consequently, this displacement has been rigorously shown to proceed with inversion of configuration at sulfur. This sequence, joined to present and earlier intercorrelations of sulfinates and sulfoxides, serves to establish absolute configurations in this series of compounds. The absolute configuration of (+)-methyl allyl sulfoxide, a key relay compound in the sequence, has been reassigned. Some apparent discrepancies which appeared in the earlier literature and which bear on the present work have been resolved.

Original languageEnglish (US)
Pages (from-to)4835-4842
Number of pages8
JournalJournal of the American Chemical Society
Volume90
Issue number18
DOIs
StatePublished - Aug 1968

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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  • Cite this

    Axelrod, M., Bickart, P., Jacobus, J., Green, M. M., & Mislow, K. (1968). The Absolute Configuration of Sulfoxides and Sulfinates. Journal of the American Chemical Society, 90(18), 4835-4842. https://doi.org/10.1021/ja01020a016