Mechanism of the Reaction of Aldehydes of the Furan Series with Secondary Amines in Methanol

Article abstract of DOI:10.1007/BF00526074

The reaction of 5-halofurfurals with piperidine and morpholine in methanol under various reaction conditions was investigated by means of spectrophotometry.The kinetics of the stepwise addition of the amine to the aldehyde function of the halofurfural were studied in the case of a dilute solution, while the conversion of the aldehyde to a 5-N,N-dialkylaminofurfurylidene-N,N-dialkylimmonium salt, for which two autocatalysis mechanisms were observed, was investigated in the case of a concentrated solution.Reaction intermediates, viz., 5-halofurfurylidene-N,N-bis(dialkylamines), were isolated preparatively and investigated.