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Abstract | Cited by

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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