N-isopropylidene-N'-2-nitrobenzenesulfonyl hydrazine, a reagent for reduction of alcohols via the corresponding monoalkyl diazenes

J Org Chem. 2007 Mar 2;72(5):1838-41. doi: 10.1021/jo062325p. Epub 2007 Feb 3.

Abstract

The reagent N-isopropylidene-N'-2-nitrobenzenesulfonyl hydrazine (IPNBSH) is used in the reduction of alcohols via the loss of dinitrogen from transiently formed monoalkyl diazene intermediates accessed by sequential Mitsunobu displacement, hydrolysis, and fragmentation under mild reaction conditions.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Crystallography, X-Ray
  • Hydrazines / chemistry*
  • Hydrolysis
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Nitrobenzenes / chemistry*
  • Reducing Agents
  • Spectroscopy, Fourier Transform Infrared
  • Stereoisomerism

Substances

  • Alcohols
  • Hydrazines
  • Indicators and Reagents
  • Nitrobenzenes
  • Reducing Agents