Acyl-isothiocyanates as efficient thiocyanate transfer reagents

Org Lett. 2009 Aug 6;11(15):3382-5. doi: 10.1021/ol901561j.

Abstract

An unprecedented transfer of a thiocyanate (-SCN) group from aroyl/acyl isothiocyanate to alkyl or benzylic bromide is observed in the presence of a tertiary amine. This process is most effective when the bromomethyl proton is less acidic, while the presence of a more acidic proton gives 1,3-oxathiol-2-ylidine and other related products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetophenones / chemistry*
  • Amines / chemistry*
  • Bromides / chemistry*
  • Isothiocyanates / chemistry*
  • Sulfhydryl Compounds / chemistry
  • Thiocyanates / chemistry*

Substances

  • Acetophenones
  • Amines
  • Bromides
  • Isothiocyanates
  • Sulfhydryl Compounds
  • Thiocyanates
  • oxathiol