Tetrahedron p. 307 - 316 (1987)
Update date:2022-09-26
Topics:
Fujio, Mizue
Funatsu, Kimito
Goto, Mutsuo
Mishima, Masaaki
Tsuno, Yuho
Rates of acetolysis of 2-aryl-2-methylpropyl p-bromobenzenesulfonates were determined for an extended series of substituents.The substituent effect can be described accurately in terms of our LArSR relationship (Yukawa-Tsuno Equation), giving an r value of 0.57.The correlation result can be reasonably accounted for on the basis of the accepted mechanism of this reaction, involving a rate-determining aryl-assisted transition state.The present study leads to the conclusion that this unique r value should be related to the resonance demand characteristic of the aryl-assisted ionization process of this reaction.The simple application of the Brown ρ?+ equation or its extended treatment and the interpretation based thereon are criticized.
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