Preparation and application of odorless 1,3-propanedithiol reagents.
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.
Matoba
Manabu
M
Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University, Misasagi, Japan.
Kajimoto
Tetsuya
T
Nishide
Kiyoharu
K
Node
Manabu
M
D002855:Chromatography, Thin Layer; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D009812:Odorants; D010084:Oxidation-Reduction; D011407:Propane / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013055:Spectrophotometry, Infrared; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D013438:Sulfhydryl Compounds; C508630:1,3-propanedithiol; D011407:Propane