an acryloyl, the acceptor), acidic C-H bonds (as present in aceto-acetate and malonate moieties, the donor), and a base catalyst strong enough to abstract the proton of this C-H bond yielding a nucleophilic carbanion
that can add to the double bond.
This result is consistent with the concept that the stabilization of aliphatic and alicyclic carbanions
is largely dependent on anionic hyperconjugation, involving the interaction between the electronic "lone pair" and antibonding C-H and C-C [[sigma].
This system performs temperature-sensitive reactions including carbohydrate chemistry, the formation of carbanions
, and other highly reactive intermediates.
In conjunction with butadiene monomer, such an organolithium based system produces allylic carbanions
that are unique in terms of their structure, reactivity and solvency.
This includes enantioselective synthesis of [Alpha]-hetereoatom stabilized carbanions
, additions of chirally-modified organometallics to carbonyl compounds, and enantioselective synthesis of natural products, particularly insect pheromones.
In the case of the sequential anionic living polymerization of (meth)acrylic monomers, it is generally known that the nucleophilic attack of polystyryl carbanions
on the caronyl group of (meth)acrylic monomer is the most usual side reaction, leading to the limited monomer conversion and branch formation.