873073-31-5Relevant articles and documents
The aminolysis of N-aroyl β-lactams occurs by a concerted mechanism
Tsang, Wing Y.,Ahmed, Naveed,Page, Michael I.
, p. 485 - 493 (2008/03/27)
N-Aroyl β-lactams are imides with exo- and endocyclic acyl centres which react with amines in aqueous solution to give the ring opened β-lactam aminolysis product. Unlike the strongly base catalysed aminolysis of β-lactam antiobiotics, such as penicillins
Competitive endo- and exo-cyclic C-N fission in the hydrolysis of N-aroyl β-lactams
Tsang, Wing Y.,Ahmed, Naveed,Hemming, Karl,Page, Michael I.
, p. 1432 - 1439 (2007/10/03)
The balance between endo- and exo-cyclic C-N fission in the hydrolysis of N-aroyl β-lactams shows that the difference in reactivity between strained β-lactams and their acyclic analogues is minimal. Attack of hydroxide ion occurs preferentially at the exocyclic acyl centre rather than that of the β-lactam during the hydrolysis of N-p-nitrobenzoyl β-lactam. In general, both endo- and exo-cyclic C-N bond fission occurs in the alkaline hydrolysis of N-aroyl β-lactams, the ratio of which varies with the aryl substituent. Hence, the Bronsted β-values differ for the two processes: -0.55 for the ring-opening reaction and -1.54 for the exocyclic C-N bond fission reaction. For the pH-independent and acid-catalysed hydrolysis of N-benzoyl β-lactam, less than 3% of products are derived from exocyclic C-N bond fission.
