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)

Abstract

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
DOIs
Publication statusPublished - 1 Mar 1987

Fingerprint

Hydrolysis
Lactams
Carbonates
Buffers
Salts
Ions
Acids
Substrates
hydroxide ion

Cite this

Page, M. I. ; Webster, P. ; Bogdan, S. ; Tremerie, B. ; Ghosez, L. / Ease of C-N Bond Cleavage in Four-membered Rings. In: Journal of the Chemical Society, Chemical Communications. 1987 ; No. 5. pp. 318-319.
@article{f0c01e116ded4dffb12423b3dc096946,
title = "Ease of C-N Bond Cleavage in Four-membered Rings",
abstract = "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.",
author = "Page, {M. I.} and P. Webster and S. Bogdan and B. Tremerie and L. Ghosez",
year = "1987",
month = "3",
day = "1",
doi = "10.1039/C39870000318",
language = "English",
pages = "318--319",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
number = "5",

}

Ease of C-N Bond Cleavage in Four-membered Rings. / Page, M. I.; Webster, P.; Bogdan, S.; Tremerie, B.; Ghosez, L.

In: Journal of the Chemical Society, Chemical Communications, No. 5, 01.03.1987, p. 318-319.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Ease of C-N Bond Cleavage in Four-membered Rings

AU - Page, M. I.

AU - Webster, P.

AU - Bogdan, S.

AU - Tremerie, B.

AU - Ghosez, L.

PY - 1987/3/1

Y1 - 1987/3/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=37049086328&partnerID=8YFLogxK

U2 - 10.1039/C39870000318

DO - 10.1039/C39870000318

M3 - Article

SP - 318

EP - 319

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 5

ER -