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].
Theoretical approach to substituent effects--structures and stabilities of carbanions XC[H.
Chapters summarize findings in the areas of reactions of aldehydes and ketones and their derivatives; reactions of carboxylic, phosphoric, and sulfonic acids and their derivatives; radical reactions; oxidation and reduction; carbenes and nitrenes; nucleophilic aromatic substitution; electrophilic aromatic substitution; carbocations; nucleophilic aliphatic substitution; carbanions
and electrophilic aliphatic substitutions; elimination reactions; polar addition reactions; cycloaddition reactions; and molecular rearrangements.
For example, studies of the superbases and carbanions
are often very sensitive to oxidation.
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.
Olefin synthesis with organic phosphonate carbanions
, Living Polymers and Electron Transfer Processes; Wiley; New York, 1968.
Use of stabilized carbanions
, ylides and enamines for carbon-carbon bond formation reactions,
, Free Radicals, Carbenes, and Nitrenes.