Effect of the leaving group and solvent in nucleophilic aliphatic substitutions promoted by quaternary onium salts

D Landini, A Maia, F Montanari…

Index: Landini, Dario; Maia, Angelamaria; Montanari, Fernando; Rolla, Franco Journal of Organic Chemistry, 1983 , vol. 48, # 21 p. 3774 - 3777

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Citation Number: 25

Abstract

Rates of nucleophilic substitutions by N3- and SCN- (as hexadecyltributylphosphonium salts) in a series of n-octyl derivatives (C8H17X, X = C1, Br, I, OTos, OMes) have been measured in different solvents (MeOH, Me,SO, PhCl, cyclohexane). Nucleofugacity scales are as follows: OTos > I > OMes 2 Br >> C1 in MeOH; I > Br > OTos > OMes > C1 in Me2SO; I > OTos N Br > OMes >> C1 in PhCl; OTos > OMes > I > Br >> C1 in cyclohexane. In the case of ...

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