Preparation and Application of Odorless 1,3-Propanedithiol Reagents

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  • Matoba Manabu
    Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University
  • Kajimoto Tetsuya
    Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University
  • Nishide Kiyoharu
    Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University
  • Node Manabu
    Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University

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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.

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