Synthesis and solvolysis of derivatives of 7-methyl-7-hydroxynorbornane and the epimeric 7-methyl-7-hydroxynorbornenes

PG Gassman, JM Pascone

Index: Gassman,P.G.; Pascone,J.M. Journal of the American Chemical Society, 1973 , vol. 95, p. 7801 - 7813

Full Text: HTML

Citation Number: 34

Abstract

Abstract: The rates of solvolysis of derivatives of 7-methyl-7-hydroxynorbornane (I), anri-7- methyl-syn-7-hydroxynorbornene (11), and syn-7-methyl-anti-7-hydroxynorbornene (111) were determined. In addition, the corresponding values for the trideuteriomethyl analogs were measured. The methyl/hydrogen rate ratio was found to vary from 1.3 x lo8 for the saturated system (I) to 4.4 x 10'for the anti-p-nitrobenzoates in the unsaturated cases (111) ...