The effect of the carbonyl and related groups on the reactivity of halides in SN2 reactions

FG Bordwell, WT Brannen

Index: Bordwell,F.G.; Brannen,W.T. Journal of the American Chemical Society, 1964 , vol. 86, p. 4645 - 4650

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Citation Number: 190

Abstract

The rates of reaction of potassium iodide in acetone solution with several series of compounds of the type YiCH?),, CI rn= 1 to* 5) have been measured. The strong deactivating effects of F, C and C6H, SOn groups when attached to the a-carbon atom are attributed to steric and field effects, their inductive effects being as-sumed to be tnildly rate enhancing. Seither these groups nor related groups, such as CaH, S, C6HjC0, or CS, ...