65862-00-2Relevant academic research and scientific papers
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.
