Preparation and application of odorless 1,3-propanedithiol reagents

Chem Pharm Bull (Tokyo). 2006 Jan;54(1):141-6. doi: 10.1248/cpb.54.141.

Abstract

2-Dodecyl-1,3-propanedithiol (2a) was prepared without a malodorous procedure as an odorless reagent that was usable in place of 1,3-propanedithiol (1) in organic reactions, e.g., in the reduction of azides and protection of carbonyl groups. The 1,3-dithioacetals obtained in the latter reaction were effectively reduced to methylene with Raney nickel and reconverted to the original carbonyl compounds by hydrolysis with N-bromosuccinimide in aqueous 2-butanone. In addition, the anion of 1,3-dithiane prepared from 2a and formaldehyde could be utilized as a synthetic equivalent of an anionic carbonyl carbon.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, Thin Layer
  • Hydrogen-Ion Concentration*
  • Hydrolysis
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Conformation
  • Odorants
  • Oxidation-Reduction
  • Propane / analogs & derivatives*
  • Propane / chemical synthesis
  • Spectrophotometry, Infrared
  • Sulfhydryl Compounds / chemical synthesis*

Substances

  • Indicators and Reagents
  • Sulfhydryl Compounds
  • 1,3-propanedithiol
  • Propane