Journal of Organic Chemistry p. 895 - 900 (1980)
Update date:2022-08-10
Topics:
Kane, Bernard J.
Marcelin, George
Traynor, Sean G.
The basicities of the alkoxides of cis- and trans-2-pinanol were examined colorimetrically and conductimetrically.The colorimetric measurements gave the following pKa values for the conjugate acids in dimethyl sulfoxide (Me2SO): 30.4, tert-butoxide; 32.5, tricyclohexylmethoxide; 32.6, cis-pinanoxide; 32.8, trans-pinanoxide.The pinanoxides are the most basic alkoxides yet measured.Conductivity measurements of Me2SO solutions containing these bases revealed that very complex equilibria processes were operative.A study of the elimination of 2-iodobutane in Me2SO with the pinanoxide bases showed a good correlation with base strength.No steric effects such as those observed with tricyclohexylmethoxide were apparent for the pinanoxide bases.
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