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
Brigas, Amadeu, F.; Clegg, William; Dillon, Christopher J.; Fonseca, Custodia F. C.; Johnstone, Robert A. W.; Brigas Amadeu, F.; UCEH, Campus de Gambelas, Universidade do Algarve; Clegg William; Department of Chemistry, University of Newcastle; Dillon Christopher J.; Department of Chemistry, University of Liverpool; Fonseca Custodia F. C.; UCEH, Campus de Gambelas, Universidade do Algarve; Department of Chemistry, University of Liverpool; Johnstone Robert A. W.; Department of Chemistry, University of Liverpool
Журнал:
Journal of the Chemical Society, Perkin Transactions 2
Дата:
2001
Аннотация:
Pseudosaccharyl and phenyltetrazolyl derivatives 1â 6 were prepared with the aim of weakening the originally strong Câ N bond in aromatic amines and facilitating its hydrogenolysis. Structural analyses of the amines 1â 6 by <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and X-ray diffraction methods have revealed major changes in Câ N bond lengths on derivatization as a result of changes in conjugation. These changes are discussed in relation to the observed reactivity of compounds 1â 6 towards catalytic and non-catalytic Câ N bond hydrogenolysis.
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