Journal of the American Chemical Society

Substituent effects and aryl participation in. beta.-(syn-9-benzonorbornenyl) ethyl p-bromobenzenesulfonate solvolyses

R Muneyuki, H Tanida

Index: Muneyuki,R.; Tanida,H. Journal of the American Chemical Society, 1968 , vol. 90, p. 656 - 662

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Citation Number: 13

Abstract

Abstract: A series of 6-substituted P-(syn-9-benzonorbornenyl) ethyl brosylates (Ia-e-OBs), the unsubstituted anti isomer (Ha-OBs), and the syn-propyl homolog (IX-OBs) were synthesized. The acetolysis of unsubstituted Ia-OBs proceeds 20 times as fast at 100'as that of IIa-OBs and yields mainly a mixture of several benzhydrindanyl derivatives formed with rearrangements. The effects of the 6 substituents on the over-all rates, koCHJkN02, ...