LITHIUM ALUMINUM HYDRIDE-N-METHYLPYRROLIDINE COMPLEX .1. SYNTHESIS AND REACTIVITY OF LITHIUM ALUMINUM HYDRIDE-N-METHYLPYRROLIDINE COMPLEX -AN AIR AND THERMALLY STABLE REDUCING AGENT DERIVED FROM LITHIUM ALUMINUM-HYDRIDE

A 1:1 lithium aluminum hydride-N-methylpyrrolidine complex (LAHNMP), o btained by the reaction of lithium aluminum hydride with N-methylpyrro lidine, is a powerful reducing agent, comparable to lithium aluminum h ydride in its reducing properties. LAHNMP reduces esters, lactones, an hydrides and carboxylic acids to the corresponding alcohols. Test redu ctions show that LAHNMP also reduces a wide range of functional groups , including amides, epoxides, oximes, nitriles, nitro compounds and ha lides. LAHNMP can be safely transferred in air with the use of a plast ic spatula and used in an open container without the need for an inert atmosphere, provided that hydrogen is not evolved during the reductio n.