Mechanism of Hydrolysis and Alcoholysis of 2-Ethoxy-N-vinylpyrrolidiniminium Tetrafluoroborate

Article abstract of DOI:10.1021/jo00190a012

N-Vinyl-2-ethoxypyrrolidiniminium tetrafluoroborate, 1, undergoes rapid hydrolysis to give acetaldehyde and ethyl 2-aminobutyrate, 2.Imidate 1 reacts with methanol or ethanol, however, to give the N-(1-alkoxyethyl)-2-alkoxypyrrolidiniminium tetrafluoroborate 7 or 9, respectively.Both hydrolysis and alcoholysis appear to be pseudo first order and the mechanism of each can be explained by initial formation of an "enamine-like" intermediate.The mechanism of both reactions is presented.