Related Experiment Video
Updated: Jun 28, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Ring opening at N1-C2 bond of azetidin-2-ones by a molybdenum hydroxo-carbonyl complex: evidence from a computational
Violeta Yeguas1, Natalia Díaz, Pablo Campomanes
1Departamento de Química Física y Analítica, Universidad de Oviedo, C/Julián Clavería, 8, 33006, Oviedo, Spain.
Abstract:
Computations on the reaction of azetidin-2-one, N-sulfonate azetidin-2-one, and 3-formylamine-N-sulfonate azetidin-2-one with [Mo(OH)(eta3-C3H5)(CO)2(N2C2H4)] were performed at the B3LYP/6-31+G(d,p) (LANL2DZ for Mo augmented by f polarization functions with exponents 1.043) taking into account solvent effects by means of the PCM-UAHF model. According to our calculations, the rate-determining energy barrier for the azetidin-2-one case, 38.0 kcal mol(-1), becomes 28.8 and 26.1 kcal mol(-1) for the N-sulfonate azetidin-2-one and 3-formylamine-N-sulfonate azetidin-2-one ones, respectively. The presence of the sulfonate group is crucial to cleave the beta-lactam N1-C2 bond by the Mo complex thanks to the interaction of the sulfonate group with the hydroxyl and bidentate ligands of the complex. This could be of interest for the synthesis of beta-amino acids and their derivatives from beta-lactams in mild conditions and low polarity solvents promoted by organometallic complexes.
Related Concept Videos
Base-Catalyzed Ring-Opening of Epoxides
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Acid-Catalyzed Ring-Opening of Epoxides
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling

