34577-76-9Relevant articles and documents
HYDROLYSIS OF CYCLIC 2-ALKOXYIMINIUM SALTS
Zezza, Charles A.,Kwon, Tae Woo,Sheu, JennLine,Smith, Michael B.
, p. 1325 - 1342 (2007/10/02)
N-Alkenyl- and N-alkoxymethyllactams are readily prepared from the corresponding lactam, and reaction with triethyloxonium tetrafluoroborate generates an 2-ethoxyiminium salt.Hydrolysis in neutral water gives the ethyl ester of 4-aminobutanoic acid (GABA) (or another ω-amino ester), an aldehyde and, in the case of the alkoxymethyl derivatives, an alcohol.The hydrolysis step requires participation of an enamine or N-alkoxymethyl moiety in a proton exchange reaction prior to fragmentation of the ring.The reaction shows a steric effect at the 'enamine' or N-alkoxymethyl terminus and some dependence on the size of the ring.The alkoxymethyl derivatives hydrolyze much slower than the alkenyllactam derivatives.
