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

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

doi:10.1039/C39940001223

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 journal › Article › peer-review

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 language	English
Pages (from-to)	1223-1224
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	10
DOIs	https://doi.org/10.1039/C39940001223
Publication status	Published - 21 May 1994

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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.",

author = "Laws, {Andrew P.} and Stone, {Julian R.} and Page, {Michael I.}",

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N2 - 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.

AB - 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.

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

Abstract

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