K. Mange, W. Middleton
Jun 1, 1989
Citations
0
Influential Citations
19
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract In contrast to most simple alcohols, cyclohexanol has proved to be a surprising difficult compound to fluorine with aminosulfur trifluorides. In the reaction of 4-morpholinosulfur trifluoride (morpho-DAST) with cyclohexanol, a correlation was found between the polarity index of the solvent, P′ , and the yield of fluorocyclohexane. In the solvents of low polarity, there appears to be an uncharged intermediate that leads to fluorocyclohexane. In solvents of higher polarity, there appears to be a charged intermediate that gives fluorocyclohexane. By a study of the fluorination of cis - and trans -4- tert -butylcyclohexanol, conformational effects were shown to be a major factor in hindering the S N 2 attack by fluoride ion on the reactive intermediates(s)