Helvetica Chimica Acta

Polar Effects. X. Polar Substituent Effects in the Solvolysis of 3??Substituted 1??Adamantyl Bromides and Toluenesulfonates

CA Grob, B Schaub

文献索引：Grob, Cyril A.; Schaub, Bruno Helvetica Chimica Acta, 1982 , vol. 65, # 6 p. 1720 - 1727

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被引用次数: 22

摘要

Abstract The rate constants for 3-substituted adamantyl p-toluenesulfonates 3a-3k in ethanol/water 80: 20 correlate well with the respective inductive substituent constants σ math image. The reaction constant ρ for the toluenesulfonates 3 is 10% larger than for the corresponding bromides 2, indicating somewhat more charge separation in the activation of the toluenesulfonates. Evidence is presented that stabilization of the resultant 1- ...