Abstract
Tertiary alcohols containing the 4,5-bis(dimethylamino)-1-naphthyl group were synthesized. The carbocations that formed from α-methyl-containing alcohols in an acidic medium underwent smooth El elimination to give the corresponding unsaturated derivatives of the “proton sponge” in good yields. At the same time, the carbocation generated from 4-(α-hydroxybenzhydryl)-1,8-bis(dimethylamino)naphthalene was converted into a benzo-[a]fluorene derivative as a result of a complex reaction which has been previously unknown in the chemistry of “proton sponges.” The structure of the latter derivative was established by X-ray diffraction analysis.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. F. Pozharskii, N. G. Tregub, E. Yu. Romanova, Z. A. Starikova, and A. I. Yanovskii,Izv. Akad. Nauk, Ser. Khim., 1999, 1311 [Russ. Chem. Bull., 1999,48, 1299 (Engl. Transl.)].
A. F. Pozharskii, N. V. Vistorobskii, M. I. Rudnev, and A. I. Chernyshev,Izv. Akad. Nauk, Ser. Khim., 1996, 2039 [Russ. Chem. Bull., 1996,45, 1934 (Engl. Transl.)].
N. V. Vistorobskii, A. F. Pozharskii, A. I. Chernyshev, and S. V. Shorshnev,Zh. Org.-Khim., 1991,27, 1037 [J. Org. Chem. USSR, 1991,27 (Engl. Transl.)].
N. V. Vistorobskii, A. F. Pozharskii, S. V. Shorshnev, and A. I. Chernyshev,Mendeleev Commun., 1991, No. 1, 10.
A. F. Pozharskii and N. V. Vistorobskii,Izv. Akad. Nauk, Ser. Khim., 1996, 1016 [Russ. Chem. Bull. 1996,45, 971 (Engl. Transl.)].
N. V. Vistorobskii, O. V. Vinogradova, and A. F. Pozharskii,Izv. Akad. Nauk, Ser. Khim., 1997, 348 [Russ. Chem. Bull., 1997,46, 334 (Engl. Transl.)].
N. V. Vistorobskii and A. F. Pozharskii,Izv. Akad. Nauk, Ser. Khim., 1996, 2297 [Russ. Chem. Bull., 1996,45, 2181 (Engl. Transl.)].
A. F. Pozharskii, G. G. Aleksandrov, and N. V. Vistorobskii,Zh. Org. Khim., 1996,32, 1049 [Russ. J. Org. Chem., 1996,32 (Engl. Transl.)].
R. C. Fuson,Adv. Organomet. Chem., 1964,1, 221.
R. M. Silverstain and G. C. Bassler, inSpectrometric Identification of Organic Compounds, J. Wiley, Inc., New York, 1968, 144.
G. A. Olah, Q. Liao, J. Casanova, R. Bau, G. Rasul and G. K. S. Prakash,J. Chem. Soc., Perkin Trans. 2, 1998, 2239.
G. A. Olah and P. V. R. Schleyer, inCarbonium Ions, Interscience, New York, 1970,II, 83.
A. Kirby and J. M. Percy,Tetrahedron, 1988,44, 6903.
G. M. Sheldrick,SHELXTL, Ver. 5.0, Software Reference Manual, Siemens Industrial Automation, Inc., Madison, 1994.
N. V. Vistorobskii and A. F. Pozharskii,Zh. Org. Khim., 1991,27, 1543 [J. Org. Chem. USSR, 1991,27 (Engl. Transl.)].
Author information
Authors and Affiliations
Additional information
For Part 26, see Ref. 1; this paper simultaneously presents Part 5 of the series “Resonance-stabilized α-naphthylmethyl carbocations and derived spiro compounds;” for Part 4, see Ref. 2.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1103–1108, June, 2000.
Rights and permissions
About this article
Cite this article
Pozharskii, A.F., Ryabtsova, O.V., Vistorobskii, N.V. et al. peri-Naphthylenediamines. Russ Chem Bull 49, 1097–1102 (2000). https://doi.org/10.1007/BF02494902
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02494902