The kinetics of the reactions of (E)‐2‐methyl‐1,3‐pentadiene (2a), 4‐methyl‐1,3‐pentadiene (2b), and (Z)‐1,3‐pentadiene (2c) with benzhydryl cations have been studied photometrically in dichloromethane solution. Substitution of these rate constants into the linear free enthalpy relationship lgk=s(N + E) yielded the nucleophilicity parameters N for these dienes. The influence of methyl groups on the nucleophilic reactivities of 1,3‐butadienes is discussed, and a system to estimate reactivities of further alkylated 1,3‐dienes is suggested.
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Mayr et al. (1996) studied this question.
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