Ease of C-N Bond Cleavage in Four-membered Rings

M. I. Page, P. Webster, S. Bogdan, B. Tremerie, L. Ghosez

Research output: Contribution to journalArticle

10 Citations (Scopus)


The hydrolysis of an azetidin-2-ylideneammonium salt gives a β-lactam and an aminoamide by competitive endo- and exo-cyclic C-N bond cleavage, the product ratio being pH and buffer dependent; the rate law for hydrolysis shows a third order term which is first order in substrate, hydroxide, and carbonate ions, which is interpreted as kinetically equivalent to general acid catalysed breakdown of the ionised tetrahedral intermediate and as evidence for non-facile C-N bond cleavage in the four-membered ring.

Original languageEnglish
Pages (from-to)318-319
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number5
Publication statusPublished - 1 Mar 1987


Cite this