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Paper | Regular issue | Vol 34, No. 7, 1992, pp.1325-1342
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6011
Hydrolysis of Cyclic 2-Alkoxyiminium Salts

Charles A. Zezza, Tae Woo Kwon, JennLine Sheu, and Michael B. Smith*

*Department of Chemistry, U-60, Rm.151, 215 Glenbrook Rd., University of Connecticut, Storrs, Connecticut 06269-3060, U.S.A.

Abstract

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 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.