Nucleophilic substitution by grignard reagents on sulfur mustards

J Org Chem. 2004 Oct 15;69(21):7336-9. doi: 10.1021/jo0489869.

Abstract

With proper activation of the leaving group, sulfur mustards react with Grignard reagents with neighboring group participation of the sulfur atom. 2,6-Dichloro-9-thiabicyclo[3.3.1]nonane is especially useful in this regard, providing clean reactivity with organomagnesium nucleophiles on a topologically constrained scaffold.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Crystallography, X-Ray
  • Indicators and Reagents / chemistry
  • Molecular Structure
  • Mustard Compounds / chemical synthesis*
  • Mustard Compounds / chemistry
  • Oxidation-Reduction
  • Stereoisomerism
  • Sulfur / chemistry*

Substances

  • Indicators and Reagents
  • Mustard Compounds
  • Sulfur