Journal of the Chemical Society. Perkin transactions II p. 1393 - 1397 (1994)
Update date:2022-08-05
Topics:
Rodriguez, J. Gonzalo
Canoira, Laureano
Cyclization of N-acetyl-N-(ortho-chlorophenyl)-4-aminobut-2-enenitrile with zerovalent nickel complexes, prepared from bis(acetylacetonate)nickel(II), with either pyridine or triphenylphosphine as ligands, and triethylaluminium as reducing agent has been carried out.The α-methylene protons show a diastereotopic effect which could be explained by a rigid bridged hydrogen bound through the oxygen atom of the acetanilide group to one of the α-methylene protons and partially hindered rotation around the N-phenyl bond, due to the ortho-substitution.Conformational analysis of the fragments of the N-3-cyanoprop-2-enyl chain has been carried out using the Sternhell treatment.
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