Reductive desulfurization of allylic thiols by HS-/H2S in water gives clue to chemical reactions widespread in natural environments.
The reduction of allylic thiols to alkenes by hydrogen sulfide in aqueous solutions, a novel reaction that may explain reduction processes widely occurring in natural environments, has been discovered. Its mechanism has been studied and suggested to follow an S(RN)1-like pathway involving radical intermediates undergoing 1,4 hydrogen shifts. [reaction: see text]
Hebting
Yanek
Y
Laboratoire de Géochimie Bioorganique, ECPM/Université Louis Pasteur, 25 rue Becquerel, 67200 Strasbourg, France.
Adam
Pierre
P
Albrecht
Pierre
P
D000475:Alkenes / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D006862:Hydrogen Sulfide / Q000737:chemistry*; D007536:Isomerism; D010084:Oxidation-Reduction; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D014867:Water / Q000737:chemistry*; D014873:Water Pollutants / Q000032:analysis*
D000475:Alkenes; D000498:Allyl Compounds; D005609:Free Radicals; D013438:Sulfhydryl Compounds; D014873:Water Pollutants; D014867:Water; D006859:Hydrogen; D006862:Hydrogen Sulfide