Abstract
The acid-catalysed rearrangement of N-acetylhydrazobenzene was shown by thin layer chromatography to yield nine products, six of them new. In the presence of anisole the condensation products6–10 are also formed, which, just as the formation of o- and p-chloroaniline when the rearrangement is conducted in the presence of hydrochloric acid, point to the intermediate formation of phenylnitrene in the course of the benzidine rearrangement or the disproportionation. The experimental evidence of phenylnitrene in its turn supports the expandedHammick theory, on the basis of which it has been predicted.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literatur
Z. J. Allan, Tetrahedron Letters1971, 4225.
M. E. Lupes, Rev. Roum. Chim.17, 1253 (1972).
G. A. Olah, K. Dunne, D. P. Kelly undY. K. Mo, J. Amer. Chem. Soc.94, 7438 (1972).
G. Tennant, Annu. Rep. Progr. ChemB 69, 236 (1972).
D. V. Banthorpe, Tetrahedron Letters1972, 2702.
H. J. Shine undJ. P. Stanley, J. Org. Chem.32, 905 (1967).
D. V. Banthorpe, A. Cooper undC. K. Ingold, Nature216, 232 (1967).
A. Reiser undL. Leyshon, J. Amer. Chem. Soc.92, 7487 (1970).
D. V. Banthorpe, R. Bramley undJ. A. Thomas, J. Chem. Soc.1964, 2900.
M. Večeřa, L. Synek undV. Štěrba, Collec. Czechosl. Chem. Commun.25, 1992 (1960).
M. Večeřa, J. Petránek undJ. Gasparič, Collect. Czechosl. Chem. Commun.22, 1603 (1957).
J. R. Cox, Jr., undM. F. Dunn, J. Org. Chem.37, 4415 (1972).
D. V. Banthorpe, undM. O'Sullivan, J. Chem. Soc. Perkin Trans. II,1973, 551.
J. H. Parish undM. C. Whiting, J. Chem. Soc.1964, 4713.
R. I. Fedorova, I. V. Obydennova, V. V. Mitina undYa. M. Paushkin, J. Prikl. Chim.46, 1079 (1973).
H. Wieland undE. Wecker, Ber. dtsch. chem. Ges.43, 699 (1910).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Allan, Z.J. Mechanismus der Benzidinumlagerung und der Disproportionierung. Abfangen des Phenylnitrens. Monatshefte für Chemie 106, 429–436 (1975). https://doi.org/10.1007/BF01150523
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01150523