On the dual reactivity of a Janus-type mesoionic dipole: experiments and theoretical validation†
Juan García
de la Concepción, 
*a
Martín
Ávalos,
a
Pedro
Cintas,
*a
José L.
Jiménez
a
and
Mark E.
Light
b
*a
Martín
Ávalos,
a
Pedro
Cintas,
*a
José L.
Jiménez
a
and
Mark E.
Light
b
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.
- This article is part of the themed collection: Mechanistic, computational & physical organic chemistry in OBC
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