Phase-Transfer Catalyzed Reactions. 5. Dramatic Effect of the Concentration of Base on the Dimerization of Crotonaldehyde

Article abstract of DOI:10.1021/jo01305a012

Self-condensation of crotonaldehyde under base-catalyzed phase-transfer conditions leads to aldehydes 3 or 4, depending only on the concentration of aqueous hydroxide used.Quaternary ammonium fluorides in anhydrous THF is shown to be a useful system for conjugate additions involving base-sensitive aldehydes.