Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

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.


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.