26356-03-6Relevant academic research and scientific papers
Pathways and Stereochemistry of Rearrangements in Reactions of Sulfenyl Chlorides with Alkenes
Borisov, A. V.,Bodrikov, I. V.,Borisova, G. N.,Smit, V. A.,Lutsenko, A. I.,Bel'skii, V. K.
, p. 943 - 951 (2007/10/03)
In reactions of 3,3-dimethyl-1-butene and 3-methyl-1-butene with 2,4-dinitrobenzenesulfenyl chloride in the systems M(ClO4)n-CH3NO2 (M=Li or Mg), 1,2 shifts of the methyl group and hydride ion respectively occur directly within the AdE process (? pathway of the rearrangement).In the same systems reactions of these alkenes with arenesulfenyl chlorides containing in the electrophilic moiety less electronegative substituents, as compared to the dinitrophenyl group, initially yield β-chloro sulfides, which under reaction conditions mostly undergo rearrangements (? pathway of the rearrangement).In nitromethane in the presence of LiClO4, AlCl3, or AgBF4 erythro-2-arylthio-1-chloro-1-deutero-2,3-dimethylbutanes are converted into stereoisomeric thiochromans; their ratio is controlled by the nature of the metal compound added, electronic properties of substituents in the arylthio moiety, and reaction temperature.
