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Alkylation of Carbonyl Compounds in Water: Formation of CC and CO Bonds in the Presence of Surfactants
Author(s) -
Cerichelli Giorgio,
Cerritelli Simona,
Chiarini Marco,
De Maria Paolo,
Fontana Antonella
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20021115)8:22<5204::aid-chem5204>3.0.co;2-c
Subject(s) - cationic polymerization , chemistry , halide , alkylation , pulmonary surfactant , electrophile , aqueous solution , ketone , hydrolysis , hydroxide , sodium hydroxide , organic chemistry , polymer chemistry , inorganic chemistry , catalysis , biochemistry
The formation of CC and CO 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.