Abstract
AbstractThe reactions of free radical addition to allylic compounds are believed to proceed the SH2′ mechanism. It is not clear whether the SH2′ mechanism is concerted or stepwise. The leaving group effects and the secondary α‐deuterium kinetic isotope effects in free radical SH2′ reactions have been determined. The leaving group effect, kBr/kCl, is from 1.88 to 14.3. The secondary α‐deuterium kinetic isotope effects, kH/kD, are 1.20 for 2‐methylallyl chloride and 1,1‐d2‐2‐methylallyl chloride and 1.22 for allyl chloride and 1,1‐d2‐allyl chloride. The free radical SH2′ reactions seem to favor the concerted mechanism.
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