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Ease of C-N bond cleavage in four-membered rings

Page, Michael I., Webster, Philip S., Bogdan, S., Tremerie, B. and Ghosez, Leon (1987) Ease of C-N bond cleavage in four-membered rings. Chemical Communications (5). pp. 318-319. ISSN 1359-7345

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The hydrolysis of an azetidin-2-ylideneammonium salt gives a -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

Item Type: Article
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Schools: School of Applied Sciences
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Depositing User: Sharon Beastall
Date Deposited: 06 Nov 2009 12:51
Last Modified: 28 Aug 2021 10:52


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