Direct Evidence for the Hydroxide Extraction Mechanism in the Phase Transfer Catalyzed Cyclopropanation of 4-Halobutyronitrile in a Solid-Liquid System

Article abstract of DOI:10.1016/S0040-4039(98)02240-0

The Hoffman degradation reaction is proposed as an unequivocal proof for the validity of the extraction mechanism in Phase Transfer Catalysis (PTC) in the presence of solid NaOH. 4-Chlorobutyronitrile is found to yield cyclopropyl cyanide via an extraction route while 4-bromobutyronitrile reacts to form the same product by the prevalent interfacial mechanism.