83249-02-9Relevant academic research and scientific papers
Synthesis of Some Bridgehead-Bridgehead-Disubstituted Bicyclopentanes
Della, Ernest W.,Taylor, Dennis K.
, p. 2986 - 2996 (2007/10/02)
The synthesis of a wide variety of 1,3-disubstituted bicyclopentanes is described, with particular emphasis on the generation of a series of 3-X-substituted bicyclopentyl bromides required for solvolytic studies.Functional group manipulation at the bridgehead was readily accomplished in the majority of cases by radical processes; in some instances, transformations were effected via carbanionic-type intermediates.
Polar Substituent Effects in 1,3-Disubstituted Bicyclopentanes
Applequist, Douglas E.,Renken, Terry L.,Wheeler, James W.
, p. 4985 - 4995 (2007/10/02)
The pKa's of eight 3-substituted bicyclopentanecarboxylic acids have been measured and found to correlate well with ?I constants.The value of ρI (2.23 +/- 0.12) is large but not large enough to propose any special perturbation of normal field-inductive effects by the close proximity (about 1.88 Ae) of the bridgehead carbons.Also determined were the products and rates of solvolyses of the p-nitrobenzoates of three 3-substituted 1-pentanes.The products were primarily unrearranged, and the rates again showed no surprisingsubstituent effects.A practical synthesis of 1,3-disubstituted bicyclopentanes has been developed and is described.
