Large Rate Enhancement for the Hydrolysis of a Four-membered Ring Phosphonamidate

Andrew P. Laws, Julian R. Stone, Michael I. Page

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Unlike β-lactams a four-membered cyclic 1,2-azaphosphetidine shows enhanced hydrolytic reactivity compared with an acyclic analogue; the cyclic phosphonamidate 3 undergoes hydroxide-ion catalysed hydrolysis in water with endocyclic P-N fission; a corresponding acyclic derivative hydrolyses with P-O fission in basic solution, the rate difference between the cyclic and acyclic structures for P-N fission is greater than 5×108.

Original languageEnglish
Pages (from-to)1223-1224
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number10
DOIs
Publication statusPublished - 21 May 1994

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