Steric assistance in the solvolysis of 2-alkyl-2-adamantyl p-nitrobenzoates

JL Fry, EM Engler, PVR Schleyer

Index: Fry,J.L. et al. Journal of the American Chemical Society, 1972 , vol. 94, p. 4628 - 4634

Full Text: HTML

Citation Number: 46

Abstract

Abstract: In order to estimate the relative importance of alkyl inductive and steric effects in the 2-adamantyl system, rates of solvolysis of a series of 2-alkyl-2-adamantyl p- nitrobenzoates were determined in 80 aqueous acetone. The relative first-order rate constants at 25” were: CH3, 1.0; C2H5; 7.7; CH2C (CH3) 3, 10.0; i-C3H7, 33.5; t-C4HQr 225,000. The solvolysis products are the unrearranged alcohols and exocyclic olefins, ...

Synthetic methods and reactions. 146. Olefins from crowded carbonyl compounds with tert-butyllithium (tert-butylmagnesium chloride)/thionyl chloride. Study of …

[Olah, George A.; Wu, An-hsiang; Farooq, Omar; Prakash, G. K. Surya Journal of Organic Chemistry, 1990 , vol. 55, # 6 p. 1792 - 1796]

Carbocationic rearrangements originating from the 2-tert-butyl-2-adamantyl system

[Saba; Fry Journal of the American Chemical Society, 1983 , vol. 105, # 3 p. 533 - 537]

Syntheses and NMR spectra of substituted 2-tert-butyladamantan-2-ols

[Duddeck, Helmut; Rosenbaum, Doris Journal of Organic Chemistry, 1991 , vol. 56, # 5 p. 1700 - 1707]