Alkali metal adducts of benzophenone azine. II. The lithium adduct

Abstract

The behavior of benzophenone azine towards lithium has been studied. Unlike sodium and potassium, lithium effected extensive reduction and cleavage of benzophenone azine; the reaction product being benzhydryl amine. By limiting the amount of lithium to 2 g-atoms per mole of azine, the reaction product was shown to be N-lithiobenzophenone imine on the basis of its chemical behavior.Two reasons are advanced to explain the behavior of lithium in contrast to that of sodium or potassium. One explanation relies upon the greater reducing power of lithium compared with the other two alkali metals. The other relies upon the tendency of organolithium compounds to associate via formation of multi-center bonds.