Vinylic cations from solvolysis. 29. Solvolysis of 9-(. alpha.-bromoarylidene) anthrones as a probe to the reactivity-selectivity relationship in solvolysis reactions

Z RapPoport, Y Apeloig…

Index: Rappoport, Zvi; Apeloig, Yitzhak; Greenblatt, Jeremy Journal of the American Chemical Society, 1980 , vol. 102, # 11 p. 3837 - 3848

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Citation Number: 22

Abstract

Abstract: The solvolyses of 9-(a-bromoarylidene) anthrones 5a (Ar= An), 5b (Ar= Tol), 5c (Ar= Ph), and 5d (Ar= o-An) in 1: l AcOH-Ac2O/NaOAc and in TFE/Z, b-lutidine and of 5a in buffered AcOH and 80% EtOH were investigated. An extensive common ion rate depression by the formed or added Br-ion was observed. Selectivity constants a= kBr-/kAcO-and a'=~ B~- /~ TFE or k~~-/ks~%~ to~ for competitive capture of the derived cations 14 by Br-vs. AcO- ...