Abstract
Barriers to racemization of the o-mono and O'-disubstituted N-phenyl ketenimines la–j were measured by dynamic NMR spectroscopy. The structures of the ketenimines 1k, 1were established by X-ray diffraction analysis. According to the experimental results and ab initio calculations (STO-3G basis set) N-aryl ketenimines and N-aryl imines in general invert their configurations by a coupled mechanism: a rotation around the N-aryl bond is coupled to inversion at nitrogen. In the transition state of nitrogen inversion the arel π system is conjugated to the p lone electron pair of the nitrogen; in the ground state, however, conjugation between the aryl system and the C=N double bond is electronically preferred but may be sterically hindered.
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