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J Org Chem. 2010 Jun 18;75(12):4300-3. doi: 10.1021/jo100350t.

Unusual aryl migration in a mesomeric betaine in the solid and liquid state: mechanistic insights into the SNAr reaction.

The Journal of organic chemistry

David Cantillo, Martín Avalos, Reyes Babiano, Pedro Cintas, José L Jiménez, Mark E Light, Juan C Palacios

Affiliations

  1. Departamento de Química Orgánica e Inorgánica, QUOREX Research Group, Facultad de Ciencias-UEX, Avda. de Elvas s/n E-06071 Badajoz, Spain. [email protected]

PMID: 20481589 DOI: 10.1021/jo100350t

Abstract

An intramolecular S(N)Ar mechanism has been identified in the unexpected aryl migration observed in a mesomeric betaine. The process changes drastically the optical and spectroscopic properties and should be a valuable model for related heteroaromatic systems.

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