A. C. Reddy, B. Narsaiah, R. V. Venkataratnam
May 1, 1996
Citations
0
Influential Citations
10
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract The effect of a trifluoromethyl group on the alkylation of pyridin-2-ones, using α-haloesters, α-haloamides, allyl halides and chloroacetonitrile, has been studied. In all cases, the corresponding 2- O -alkylated products were obtained exclusively, irrespective of the nature of alkylating agent. The study indicates that the trifluoromethyl group present at the 4 or 6 position of the pyridin-2-one ring enhances the charge density on the 2-oxo group leading to the exclusive formation of O -alkylated products. If the electronic effect induced by the 4-trifluoromethyl group is mitigated by a 6-methyl substituent, the result is a mixture of N - and O -alkylated products, in conformity with the proposed rationalisation.