Abstract
AbstractA survey is given of the possible reactions between alkanes and protons or carbonium ions and in addition new kinetic data for some of these electrophilic aliphatic substitutions, including the hydrogen‐deuterium exchange in mono‐deuteroethane, and the cleavage of 2,2,3,3‐tetramethylbutane into isobutane and tert‐butyl cation. Comparison of present and former results shows that, when the proton is the electrophilic agent, electronic substituent effects predominate over steric effects. Electrophilic substitution at alkane‐carbon is likely to involve a retention of configuration, which implies a C8‐type geometry for the transition state.That the proton reactivity is lower in FHSO3‐SbF5 than in HF‐SbF5 is probably due to the lower acidity of the former solvent system.
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