PHASE-TRANSFER CATALYZED ALKYLATION OF PYRAZOLES AND 1,2,4-TRIAZOLE WITH cis- AND trans-1,4-DICHLORO-2-BUTENES

Article abstract of DOI:10.1007/BF00480755

The phase-transfer catalyzed (PTC) alkylation of pyrazoles and 1,2,4-triazole with cis- and trans-1,4-dichloro-2-butenes (DCB) has been examined.The monoalkylation products of pyrazoles with cis-DCB are bicyclic salts formed by intramolecular cyclization of the intermediate cis-1-(4-chloro-2-butenyl)pyrazoles.The corresponding trans-compounds are incapable of cyclization, but on prolonged standing they undergo intermolecular polyquaternization.Both cis- and trans-DCB undergo phase-transfer catalyzed reaction with 1,2,4-triazole to give polymeric quaternary salts.Conditions have been worked out for the dehydrochlorination of 1-(4-chloro-2-butenyl)azoles to 1-(butadien-2-yl)azoles.