Journal of the American Chemical Society

Solvolyses of tertiary. alpha.-arylcycloalkyl and-polycycloalkyl chlorides. Effects of ring size and substituents in the aryl ring on the solvolysis rates

H Tanida, T Tsushima

Index: Tanida,H.; Tsushima,T. Journal of the American Chemical Society, 1970 , vol. 92, p. 3397 - 3403

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Citation Number: 32

Abstract

Abstract: A series of a-arylcyclobutyl (1-Z),-cyclopentyl (2-Z),-cyclohexyl (3-, Z),-7-norbornyl (4-Z), and-2-adamantyl (5-2) chlorides, in which the aryl rings are variously substituted for the study of substituent effects, was prepared and their solvolysis rates in 90% aqueous acetone were studied. The reactivities decrease in the sequence 2-2> 5-2> t-cumyl chlorides (6-2)> 1-2-3-2> 4-2; and for the parent a-phenyl (R= H) compounds, the relative rates at ...