Reaction products and mechanism of the regioselective oxidation of N-phenylmorpholine by ozone |
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Authors: | Ricardo Suarez-Bertoa Francesco Saliu Maurizio Bruschi Bruno Rindone |
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Affiliation: | Department of Environmental Sciences, University of Milano-Bicocca, Piazza della Scienza 1, 20126 Milano, Italy |
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Abstract: | The regioselective oxidation of N-phenylmorpholine by ozone in dichloromethane or acetonitrile produced a lactam and a diformylderivative. These products derive from the selective attack of ozone at the heterocyclic ring in one of the two non-equivalent reactive carbons. The reaction mechanism has been investigated by DFT calculations, which show that the reaction occurs through the insertion of ozone at the carbon–hydrogen bond of a methylene group of the morpholine ring. The regioselectivity is due to the significantly lower energy barrier calculated for the attack of ozone α to nitrogen than α to oxygen. In addition, the energy barrier decreases with increasing the polarity of the solvent, explaining the higher conversions observed for the reaction carried out in acetonitrile than in dichloromethane. |
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