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

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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

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Publication details

The article was received on 21 May 2018, accepted on 06 Jun 2018 and first published on 06 Jun 2018


Article type: Communication
DOI: 10.1039/C8OB01195H
Citation: Org. Biomol. Chem., 2018, Advance Article
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    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, Advance Article , DOI: 10.1039/C8OB01195H

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