NITROGEN INVERSION AND N-O BOND ROTATION IN SOME HYDROXYLAMINE AND ISOXAZOLIDINE DERIVATIVES

A series of trisubstituted hydroxylamine derivatives, both cyclic and acyclic, has been prepared, The energy barriers in these hydroxylamine s are found to be dominated either by nitrogen inversion or N-O bond r otation depending on the nature of the substituents attached to the ni trogen. In several series of compounds, having XC(6)H(4)CH(2) substitu ents attached to nitrogen, Hammett free energy correlations are obtain ed with positive rho values, indicating increased electron density at the transition state for the inversion process, Isoxazolidines with C( 5) ethoxy substituents demonstrate a strong anomeric effect.