The Journal of Organic Chemistry

Sodium-and Potassium-Catalyzed Reactions of Toluene, Ethylbenzene, and Isopropylbenzene with Isoprene1, 2

H Pines, NC Sih

Index: Pines,H.; Sih,N.C. Journal of Organic Chemistry, 1965 , vol. 30, p. 280 - 284

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Citation Number: 16

Abstract

In the sodium-and potassium-catalyzed alkenylation of alkylarenes with isoprene, the mode of addition seems to be determined by the relative stabilities of the resultant carbanions and also the" size effect" of alkali metal ions in the transition state. The ratios of monoadducts resulting from" head addition" and" tail addition" are 2.77, 1.88, and 1.98 for toluene, ethylbenzene, and isopropylbenzene, respectively, in the presence of sodium; and 3.04, ...

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