Syntheses are reported for p-bicyclo[2,2,2]octan-1-yl-, and p-adamantan-1-yl-benzoic acids and for the corresponding -2-chloropropanes. Determination of acidities and hydrolysis rates of these compounds gives σp values of –0·25 and –0·24 and σp+ values of –0·27 and –0·25 for the bicyclo-octanyl and adamantanyl substituents. This virtual lack of enhancement of σ values is discussed.
T. J. Broxton, G. Capper, L. W. Deady, A. Lenko and R. D. Topsom, J. Chem. Soc., Perkin Trans. 2, 1972, 1237 DOI: 10.1039/P29720001237
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