Metal-assisted reactions. Part 29. Structure and hydrogenolysis of C-N bonds in derivatives of aromatic amines. Bond length and electronegativity changes from X-ray crystallographic data
Af. Brigas et al., Metal-assisted reactions. Part 29. Structure and hydrogenolysis of C-N bonds in derivatives of aromatic amines. Bond length and electronegativity changes from X-ray crystallographic data, J CHEM S P2, (8), 2001, pp. 1315-1324
Citations number
58
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Pseudosaccharyl and phenyltetrazolyl derivatives 1-6 were prepared with the
aim of weakening the originally strong C-N bond in aromatic amines and fac
ilitating its hydrogenolysis. Structural analyses of the amines 1-6 by H-1
and C-13 NMR spectroscopy and X-ray diffraction methods have revealed major
changes in C-N bond lengths on derivatization as a result of changes in co
njugation. These changes are discussed in relation to the observed reactivi
ty of compounds 1-6 towards catalytic and non-catalytic C-N bond hydrogenol
ysis.