On the dual reactivity of a Janus-type mesoionic dipole: experiments and theoretical validation
Juan García de la Concepción1, Martín Ávalos, Pedro Cintas
1Departamento de Química Orgánica e Inorgánica, Facultad de Ciencias-UEX, IACYS-Unidad de Química Verde y Desarrollo Sostenible, E-06006 Badajoz, Spain. jugarco@unex.es.
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.
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