Issue 26, 2018

On the dual reactivity of a Janus-type mesoionic dipole: experiments and theoretical validation

Abstract

A mesoionic bicycle, easily synthesized from a proteinogenic amino acid, L-leucine, behaves as both thiazolium-olate and diazolium-olate dipoles, as unveiled by its dipolar cycloadditions. This chameleonic reactivity has been thoroughly interpreted by dissecting the mechanistic landscape aided by the distortion–interaction model.

Graphical abstract: On the dual reactivity of a Janus-type mesoionic dipole: experiments and theoretical validation

Supplementary files

Article information

Article type
Communication
Submitted
21 mai 2018
Accepted
06 juin 2018
First published
06 juin 2018

Org. Biomol. Chem., 2018,16, 4778-4783

On the dual reactivity of a Janus-type mesoionic dipole: experiments and theoretical validation

J. G. de la Concepción, M. Ávalos, P. Cintas, J. L. Jiménez and M. E. Light, Org. Biomol. Chem., 2018, 16, 4778 DOI: 10.1039/C8OB01195H

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