A Theoretical and Experimental Perspective on the Stereochemistry of 1,3-Diazepan-2-ylidenes
Related Experiment Video
Updated: Oct 31, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
Ana J Ferrugini Souza1, Matheus P Freitas2, Diego P Sangi1
1Universidade Federal Fluminense, Departamento de Química, Instituto de Ciência Exatas, Rua Ellis Hermydio Figueira, 783, Aterrado, 27213-145 Volta Redonda, RJ, Brazil.
Abstract:
Diazepine compounds are well known for their broad range of biological activities and diverse applications. However, 1,3-diazepan-2-ylidenes remain unexplored in the literature. These compounds possess intriguing structural features that make them excellent candidates for studying rotational barriers associated with the resonance of the ketene moiety and the N1, N3 atoms, as well as electron-withdrawing substituents. NMR experiments conducted at room temperature suggest that the rotational barrier is sufficiently low to allow interconversion between conformers, or that the conformers are so similar that their signals cannot be resolved. Computational calculations were performed to estimate the rotational barrier, and additional NMR experiments were carried out at subambient temperatures in an attempt to separate the overlapping signals. All results support the hypothesis that the observed spectra arise from unresolved conformational overlap.
More Related Videos
Related Concept Videos
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Stereoisomerism of Cyclic Compounds
Radical Halogenation: Stereochemistry
Halogenation to form a new chiral center:
Diazonium Group Substitution: –OH and –H
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)