Alkylation of carbonyl compounds in water: formation of C-C and C-O bonds in the presence of surfactants.
The formation of C-C and C-O bonds by the reaction of enolate intermediates with electrophilic substrates commonly requires strong bases, aprotic solvents and very low temperatures. A way of performing the same reactions with sodium hydroxide at moderate temperatures in aqueous surfactant solutions is presented. Different halides, ketones and surfactants (cationic, zwitterionic and anionic) have been used. The results obtained show that the amount of ketone alkylation is much higher and that the reactions are faster in the presence than in the absence of surfactant aggregates. The hydrolysis of the halide is minimised in the presence of cationic or zwitterionic surfactants.
Cerichelli
Giorgio
G
Dipartimento di Chimica, Ingegneria Chimica e Materiali Università degli Studi dell'Aquila via Vetoio-Coppito due, 67010 L'Aquila, Italy. cerichel@univaq.it
Cerritelli
Simona
S
Chiarini
Marco
M
De Maria
Paolo
P
Fontana
Antonella
A