Allylic Organometallic Reagents Useful Three-Carbon Nucleophiles

ALLYLIC ORGANOMETALLIC REAGENTS USEFUL THREE-CARBON NUCLEOPHILES 

Propene is appreciably more acidic than propane because of the relative stability of the conjugated carbanion that results from deprotonation (Section 14-1). Therefore, allylic lithium reagents can be made from propene derivatives by proton abstraction by an alkyllithium. The process is facilitated by A,A,A, Al -tetramethylethane-l,2-diamine (telramethylethylenediamine, TMEDA), a good solvating agent. 

---