20259-37-4Relevant academic research and scientific papers
FLUORINATION OF CYCLOHEXANOLS WITH 4-MORPHOLINOSULFUR TRIFLUORIDE
Mange, Kevin C.,Middleton, W. J.
, p. 405 - 414 (1989)
In contrast to most simple alcohols, cyclohexanol has proved to be a surprisingly difficult compound to fluorinate 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 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 SN2 attack by fluoride ion on the reactive intermediate(s).
THE REACTION OF PERFLUOROBUTANESULFONYL FLUORIDE WITH ALCOHOLS IN THE PRESENCE OF 4-DIALKYLAMINOPYRIDINES
Bennua-Skalmowski, Baerbel,Krolikiewicz, Konrad,Vorbrueggen, Helmut
, p. 453 - 462 (2007/10/02)
Primary hydroxy groups as in neopentyl alcohol 7 or neopentylglycol 18 react readily with perfluorobutanesulfonyl fluoride 1 in the presence of 2 equiv. of the nucleophilic 4-dialkylaminopyridines 4 to afford high yields of the corresponding N-alkyl-4-dialkylaminopyridinium perfluorobutanesulfonates (nonaflates).Secondary hydroxy groups give rise to a mixture of the corresponding olefins and monofluorides as well as of the corresponding N-alkyl-4-dialkylaminopyridinium nonaflates.
