3,3- ˛-N,N- ˛-Bis (amino) -2,2- ˛-bipyridine - An unusually methylation-resistant amine
Chisholm, D.M.; McDonald, R.; McIndoe, J.S.
Canadian Journal of Chemistry 89(8): 971-977
2011
ISSN/ISBN: 0008-4042 DOI: 10.1139/v11-066
Accession: 080891044
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Summary
Methylation of aromatic amino groups is usually straightforward, but the formation of two intramolecular hydrogen bonds in 3,3′-N,N′-bis(amino)-2,2′-bipyridine and (or) the potential for ring methylation prevents the clean tetramethylation of this molecule. Numerous attempts to make 3,3′-N,N′-bis(dimethylamino)-2,2′-bipyridine produced only complex mixtures of variously methylated products, and the only isolated molecule was 3,3′-N,N′-bis(methylamino)-2,2′-bipyridine, for which an X-ray crystal structure was obtained.References
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