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

Fingerprint

Lactams
Hydrolysis
Water
Derivatives
Ions
hydroxide ion

Cite this

@article{c0ddf4ba059843a695bb2f145b184609,
title = "Large Rate Enhancement for the Hydrolysis of a Four-membered Ring Phosphonamidate",
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.}",
year = "1994",
month = "5",
day = "21",
doi = "10.1039/C39940001223",
language = "English",
pages = "1223--1224",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
number = "10",

}

Large Rate Enhancement for the Hydrolysis of a Four-membered Ring Phosphonamidate. / Laws, Andrew P.; Stone, Julian R.; Page, Michael I.

In: Journal of the Chemical Society, Chemical Communications, No. 10, 21.05.1994, p. 1223-1224.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Large Rate Enhancement for the Hydrolysis of a Four-membered Ring Phosphonamidate

AU - Laws, Andrew P.

AU - Stone, Julian R.

AU - Page, Michael I.

PY - 1994/5/21

Y1 - 1994/5/21

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.

UR - http://www.scopus.com/inward/record.url?scp=37049082808&partnerID=8YFLogxK

U2 - 10.1039/C39940001223

DO - 10.1039/C39940001223

M3 - Article

SP - 1223

EP - 1224

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 10

ER -