The Journal of Organic Chemistry

Solvolysis of allyl arenesulfonates. Cautionary comments concerning the NOTs scale of solvent nucleophilicities

DN Kevill, TJ Rissmann

文献索引：Kevill, Dennis N.; Rissmann, Thomas J. Journal of Organic Chemistry, 1985 , vol. 50, # 17 p. 3062 - 3064

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被引用次数: 18

摘要

The rates of solvolysis of five allyl arenesulfonates are analyzed in terms of the extended Grunwald-Winstein equation. The 1 values are constant but the m values decrease slightly as the nucleofugality of the leaving group increases. The solvent nucleophilicity (NOTs) values presently available in the literature are based upon am value for methyl p- toluenesulfonate (tosylate) solvolysis of 0.3; it is demonstrated that a value of 0.55 is more ...