The Structures of Organolithium Compounds

Abstract

Publisher Summary This chapter describes the structures of organolithium and related compounds. The implications of structural considerations for an understanding of the mechanisms of organolithium reactions are also discussed. The organolithium compounds are members of a larger class that is often referred to as electron deficient and includes Group II and III organometallic compounds, boron hydrides, and others. Electron deficiency is characterized by the formation of polymeric species through the delocalization of one or more bonding electron pairs. Organolithium compounds vary widely in reactivity, but all are vigorously reactive with both air and moisture. These compounds may also interact with bases by dissociating. Typical adducts formed in this way are proposed on the basis of kinetic or colligative property data obtained upon the addition of the base to hydrocarbon solutions of the alkyllithium compounds. Both alkyl and aryllithium compounds are capable of reacting with other organometallic compounds to form mixed species of well-defined stoichiometry that may or may not contain coordinated solvent. The chapter discusses the kinetics and mechanisms of the organolithium reactions, where the association of alkyllithium compounds with hydrocarbon solvents and the effect of bases on alkyllithium kinetics are discussed.