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

Author:

de la Concepción Juan García12345ORCID,Ávalos Martín12345ORCID,Cintas Pedro12345ORCID,Jiménez José L.12345ORCID,Light Mark E.6789ORCID

Affiliation:

1. Departamento de Química Orgánica e Inorgánica

2. Facultad de Ciencias-UEX

3. IACYS-Unidad de Química Verde y Desarrollo Sostenible

4. E-06006 Badajoz

5. Spain

6. Department of Chemistry

7. University of Southampton

8. Southampton SO17 1BJ

9. UK

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.

Funder

European Regional Development Fund

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Reference36 articles.

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2. Aldehyde N , N ‐Dialkylhydrazones as Neutral Acyl Anion Equivalents: Umpolung of the Imine Reactivity

3. F. Tanaka and C. F.BarbasIII , in Enantioselective Organocatalysis: Reactions and Experimental Procedures , ed. P. I. Dalko , Wiley-VCH , Weinheim , 2007 , ch. 2, pp. 19–55

4. Orthogonal Reactivity of Acyl Azides in C–H Activation: Dichotomy between C–C and C–N Amidations Based on Catalyst Systems

5. New RuIIComplex for Dual Activity: Photoinduced Ligand Release and1O2Production

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