Steric effects in five-membered rings. Part VI. Kinetics of oxidation of β-substituted cyclopentanols by chromium(VI) oxide

Abstract

A study is presented on the Cr^VI oxidation rates of 3,3- and 3,3,4,4-substituted cyclopentanols at four temperatures. The activation parameters were evaluated. Kinetic isotope effects were also measured at all temperatures. Mechanistic and conformational implications are discussed and it is concluded that, in contrast to analogous six-membered ring compounds, the behaviour of cyclopentanols indicates lack of appreciable non-bonded interactions and the operation of torsional strain relief.