Amination reactions of alkoxymidolithium compounds; an ab initio S.C.F. M. O. model involving an (N–O)-lithium-bridged intermediate

Abstract

Ab initio S.C.F. M.O. calculations indicate that the reaction of alkoxyamidolithium LiRN–OR¹ with an organolithium R²Li to give LiOR¹ and LiRNR² proceeds via an intermediate in which the N–O bond is lithium-bridged and hence is longer than in the precursor alkoxyamine; such a structure is thereby ‘primed’ for LiOR¹ elimination and N–R² bond formation, and accordingly seems more apt than a recently proposed one obtained from MNDO calculations in which both Li atoms are terminally attached to the nitrogen.