Abstract
Unlike cyclic aliphatic nitroxyls, whose oxidation with halogens gives oxoammonium salts, bis(4-tert-butylphenyl)amine-N-oxyl (1) treated with chlorine undergoes reductive chlorination to the corresponding di- and trichlorodiphenylamines. Chlorine partially dealkylates the compounds obtained. Plausible mechanisms for these reactions were suggested.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
V. A. Golubev, Yu. N. Kozlov, A. N. Petrov, A. P. Purmal’, in Nitroksil’nye radikaly: sintez, khimiya, prilozheniya [Nitroxyl Radicals: Synthesis, Chemistry, Application], Eds E. G. Rozantsev, R. I. Zhdanov, Nauka, Moscow, 1987, 56 pp. (in Russian).
A. E. J. Nooy, A. C. Besemer, H. van Bekkum, Synthesis, 1996, 1153.
N. Merbouh, J. M. Bobbitt, C. Bruckner, Org. Prep. Proc. Int., 2004, 36, 1.
G. Tojo, M. Fernandez, Oxidation of Alcohols to Aldehydes and Ketones, Springer, New York, 2006, 241pp.
J. M. Bobbitt, C. Bruckner, N. Merbouh, Organic Reactions, 2009, 74, 103.
R. Gnehm, Chem. Ber., 1875, 8, 1040.
K. H. Meyer, W. Reppe, Chem. Ber., 1921, 54, 327.
V. A. Golubev, V. D. Sen’, Russ. J. Org. Chem. (Engl. Transl.), 2013, 49, 555 [Zh. Org. Khim., 2013, 49, 572].
G. Kostrab, M. Lovic, I. Janotka, M. Bajus, D. Mravec, Appl. Catal. A, 2008, 335, 210.
A. W. Chapman, J. Chem. Soc., 1929, 571.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2074–2078, September, 2013.
Rights and permissions
About this article
Cite this article
Golubev, V.A., Sen’, V.D. Reductive chlorination of bis(4-tert-butylphenyl)amine-N-oxyl nitroxyl radical. Russ Chem Bull 62, 2074–2078 (2013). https://doi.org/10.1007/s11172-013-0300-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-013-0300-1