Chemistry Letters p. 2065 - 2068 (1991)
Update date:2022-08-17
Topics:
Shimizu, Nobujiro
Tsutsumi, Toru
Tsuno, Yuho
Solvent effect on the cyclization of 4-hydroxy-4-methyl-1-pentyl p-toluenesulfonate, a mechanistic equivalent to the SN2 solvolysis, was successfully analyzed by Taft LSER equation as log k=3.2?*+1.4α+1.9β-8.36, indicating that three independent factors are operative, i.e., solvent polarity and H-bond donor ability which promote ionization, and H-bond acceptor ability which enhances nucleophilicity of the internal OH group.
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