Croatica Chemica Acta, Vol. 65 No. 3, 1992.
Original scientific paper
Solvolysis of 1-(3-Noradamantyl)-2-methylpropyl and 1-(3-Noradamantyl)-2,2-dimethylpropyl Pemsylates
D. T. Stoelting
; Department of Chemistry, Indiana University, Bloomington, Indiana 47405
V. J. Shiner, Jr.
; Department of Chemistry, Indiana University, Bloomington, Indiana 47405
Abstract
Rates, m-values, a-d and ft-d rate effects are reported for solvolyses of the title esters along with MMX calculations of the strain energies of initial and transition states. These results are compared with those from several lower homologs and related adamantyl carbinyl esters. It is found that the noradamantyl carbinyl ester solvolyses are accelerated up to 10,000-fold by C-C o-participatìon; /3-branching in
the alkyl side-chain reduces this rate effect by as much as 100-fold.
Keywords
Hrčak ID:
137113
URI
Publication date:
15.10.1992.
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