Permanganate Ion Oxidations. 19. Hexadecyltrimethylammonium Permanganate Oxidation of Cycloalkenes

Article abstract of DOI:10.1021/jo00272a051

The kinetics of hexadecyltrimethylammonium permanganate (cetyltrimethylammonium permanganate, CTAP) oxidation of cycloalkenes in dichloromethane have been studied.The relative rates of oxidation versus 13C NMR chemical shifts, vertical ionization potentials, and strain energies are discussed.A comparison of the relative rate of permanganate ion oxidation with the relative rates of addition of other reagents to carbon-carbon double bonds suggests that it may act as a 1,3-dipole.