90976-72-0Relevant academic research and scientific papers
The Interaction of Arenesulphonyl Chlorides, Aluminium Chloride, and Saturated Alicyclic Hydrocarbons containing at least One Tertiary Hydrogen Atom
Ewedemi, Rotimi O.,Fields, Roy,Holt, Geoffrey
, p. 1466 - 1500 (2007/10/02)
Cycloalkanes having at least one tertiary hydrogen react with a mixture of benzenesulphonyl chloride and aluminium chloride in carbon disulphide, with reactivity decreasing in the order cis-decalin ca. cis-hexahydroindane > trans-decalin >/= dicyclohexyl > methylcyclohexane > t-butylcyclohexane > methylcyclopentane.Although hydrogen chloride was evolved and benzenesulphonyl chloride was reduced to benzenesulphinic acid in all the reactions, only cis-decalin, and, to a much smaller extent, dicyclohexyl, gave appreciable amounts of chloro- or dichloro-cycloalkanes.In other reactions the major products were hydrocarbon "dimers" and "trimers" apparently formed by attack by the carbenium ion on cycloalkenes formed in the reaction.Electron-attracting substituents in the arenesulphonyl chloride enhanced the rate of reaction with cis-decalin, and electron-donor substituents retarded the reaction, which appears to proceed via hydride-ion abstraction by the arenesulphonyl halide-aluminium halide "oxonium complex" rather than by the (+) ion.
