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Chu T, Vyboishchikov SF, Gabidullin BM, et al. Oxidative Cleavage of the C═N Bond on Al(I). J Am Chem Soc. 2017;139(26):8804-8807doi: 10.1021/jacs.7b04841.
Chu, T., Vyboishchikov, S. F., Gabidullin, B. M., & Nikonov, G. I. (2017). Oxidative Cleavage of the C═N Bond on Al(I). Journal of the American Chemical Society, 139(26), 8804-8807. https://doi.org/10.1021/jacs.7b04841
Chu, Terry, et al. "Oxidative Cleavage of the C═N Bond on Al(I)." Journal of the American Chemical Society vol. 139,26 (2017): 8804-8807. doi: https://doi.org/10.1021/jacs.7b04841
Chu T, Vyboishchikov SF, Gabidullin BM, Nikonov GI. Oxidative Cleavage of the C═N Bond on Al(I). J Am Chem Soc. 2017 Jul 05;139(26):8804-8807. doi: 10.1021/jacs.7b04841. Epub 2017 Jun 21. PMID: 28608679.
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J Am Chem Soc. 2017 Jul 05;139(26):8804-8807. doi: 10.1021/jacs.7b04841. Epub 2017 Jun 21.

Oxidative Cleavage of the C═N Bond on Al(I).

Journal of the American Chemical Society

Terry Chu, Sergei F Vyboishchikov, Bulat M Gabidullin, Georgii I Nikonov

Affiliations

  1. Department of Chemistry, Brock University , 1812 Sir Isaac Brock Way, St. Catharines, Ontario Canada L2S 3A1.
  2. Institut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona , Carrer Maria Aurèlia Capmany 69, 17003 Girona, Spain.
  3. X-Ray Core Facility, Faculty of Science, University of Ottawa , 150 Louis Pasteur, Ottawa, Ontario, Canada K1N 6N5.

PMID: 28608679 DOI: 10.1021/jacs.7b04841

Abstract

Reaction of the cyclic guanidine TolN═SIMe with the aluminum(I) compound NacNacAl (1) results in the unprecedented cleavage of the C-N multiple bond to give, after rearrangement, the carbene-ligated Al(III) amide, NacNac'Al(NHTol)(SIMe) (6). DFT calculations revealed that these reactions proceed via a bimolecular mechanism in which either the basic Al(I) center or the transient Al═NTol species deprotonates the methyl group of the NacNac ligand.

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