Synthesis of 8-(dimethylamino)-1-naphthyllithium etherate. Its structure in the solid (X-ray) and in Solution (7Li and 1H NMR)

Abstract

The reaction of Bu{4}Li{4} with 4 molar equivalents of 1-(dimethylamino)naphthalene in diethyl ether affords novel 8-(dimethylamino)-1-naphthyllithium. Its molecular structure (X-ray) consists of two 8-(dimethylamino)-1-naphthyl groups each 3 center-2 electron bonded via C(1) to two lithium atoms and via the nitrogen lone pair to one of these lithium atoms. Diethyl ether coordination completes the pseudo tetrahedral lithium coordination sphere. Variable temperature }7{Li and }1{H NMR spectroscopy reveals an equilibrium between the [8-Me{2}NC{1}{0}H{6}Li.OEt{2}]{2} species and the ether-free [8-Me{2}NC{1}{0}H{6}Li]{n}. A tetranuclear structure is proposed for the latter species.