Issue 60, 2013
From the journal:

Chemical Communications

Dibenzyl and diallyl 2,6-bisiminopyridinezinc(ii) complexes: selective alkyl migration to the pyridine ring leads to remarkably stable dihydropyridinates†

John J. Sandoval,a   Pilar Palma,a   Eleuterio Álvarez,a   Antonio Rodríguez-Delgado*a  and  Juan Cámpora*a  

* Corresponding authors

a Instituto de Investigaciones Químicas, CSIC - Universidad de Sevilla, c/Americo Vespucio 49, Sevilla, Spain
E-mail: campora@.iiq.csic.es, arodriguez@us.es
Fax: +34 954460565
Tel: +34 954489555

Abstract

Diorganozinc compounds (ZnR2) with R = CH2Ph or CH2CH[double bond, length as m-dash]CH2 react with 2,6-bisiminopyridines (iPrBIP) to afford thermally stable dihydropyridinate(−1) complexes, and do not react if R = CH2SiMe3 or CH2CMe2Ph. NMR studies reveal that dibenzylzinc binds iPrBIP at −80 °C, yielding the unstable complex [Zn(CH2Ph)2(iPrBIP)]. Above −20 °C, this undergoes selective alkyl migration to the remote 4 position of the central pyridine ring.

Graphical abstract: Dibenzyl and diallyl 2,6-bisiminopyridinezinc(ii) complexes: selective alkyl migration to the pyridine ring leads to remarkably stable dihydropyridinates

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Article information

DOI
https://doi.org/10.1039/C3CC42798F
Article type
Communication
Submitted
16 Apr 2013
Accepted
06 Jun 2013
First published
07 Jun 2013
This article is Open Access

Chem. Commun., 2013,49, 6791-6793

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Dibenzyl and diallyl 2,6-bisiminopyridinezinc(II) complexes: selective alkyl migration to the pyridine ring leads to remarkably stable dihydropyridinates

J. J. Sandoval, P. Palma, E. Álvarez, A. Rodríguez-Delgado and J. Cámpora, Chem. Commun., 2013, 49, 6791 DOI: 10.1039/C3CC42798F

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