DABCO-bis(sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: utility in sulfonamide and sulfamide preparation

Org Lett. 2011 Sep 16;13(18):4876-8. doi: 10.1021/ol201957n. Epub 2011 Aug 25.

Abstract

The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as a replacement for gaseous sulfur dioxide. The complex can be combined with Grignard reagents to form sulfinates, which can then be converted in situ to a series of sulfonamides. Alternatively, reaction with anilines and iodine leads to the formation of a series of sulfamides. Cheletropic addition between DABSO and 2,3-dimethylbutadiene provides the corresponding sulfolene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Structure
  • Piperazines / chemistry*
  • Stereoisomerism
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfur Dioxide / chemistry*

Substances

  • Piperazines
  • Sulfonamides
  • Sulfur Dioxide
  • triethylenediamine