Abstract
The first one-pot N-acylations and N-alkylations of o-nitroaniline with saturated hydrocarbons were performed in the presence of superelectrophiles; the role of CO in the alkylation with n-pentane is discussed.
References
1.
G. A. Olah and G. K. S. Prakash, Electrophile Reactions of Alkanes. The Chemistry of Alkanes and Cycloalkanes, eds. S. Patai and Z. Rappoport, Wiley-Interscience, Chichester–New York, 1992, ch. 13.
2.
C. L. Hill, Activation and Functionalization of Alkanes, Wiley-Interscience, New York, 1989.
3.
New J. Chem. (Special Issue on Alkane Activation and Functionalization), 1989, 13, 645.
4.
J. Organomet. Chem. (Special Issue on Aspects of C–H Activation), 1995, 504, 1 and references cited therein.
5.
Shilov A.E., Shul'pin G.B.
Chemical Reviews,
1997
6.
7.
10.1016/j.mencom.2010.09.005_bib0015_2
Labinder
Nature,
2002
8.
I. S. Akhrem, A. V. Orlinkov, E. I. Mysov and M. E. Vol’pin, Tetrahedron Lett., 1981, 22, 3891.
9.
Akhrem I.S., Orlinkov A.V., Vol'pin M.E.
Russian Chemical Reviews,
1996
10.
Akhrem I.S., Orlinkov A.V.
Russian Chemical Bulletin,
1998
11.
I. S. Akhrem, Izv. Akad. Nauk, Ser. Khim., 2003, 2466 (Russ. Chem. Bull., Int. Ed., 2003, 52, 2606).
12.
Akhrem I., Orlinkov A.
Chemical Reviews,
2007
13.
10.1016/j.mencom.2010.09.005_bib0025_1
Mahy
New J. Chem.,
1989
14.
Gómez-Emeterio B.P., Urbano J., Díaz-Requejo M.M., Pérez P.J.
Organometallics,
2008
15.
Kovacic P., Roskos P.D.
Tetrahedron Letters,
1968
16.
P. Kovacic and Ph. D. Roskos, J. Am. Chem. Soc. 1969, 91, 6457.
17.
Volkova S.B., Platonova O.V., Tsypin V.G., Polukeev V.A.
Russian Journal of General Chemistry,
2008
18.
10.1016/j.mencom.2010.09.005_bib0035_1
Haaf
73, 144;,
1961
19.
OHSUGI M., INAMOTO Y., TAKAISHI N., FUJIKURA Y., AIGAMI K.
Synthesis,
1977
20.
Olah G.A., Balaram Gupta B.G.
Journal of Organic Chemistry,
1980
21.
Akhrem I.S., Avetisyan D.V., Afanas’eva L., Vitt S.V., Petrovskii P.V., Orlinkov A.
Tetrahedron Letters,
2008
22.
Tafesh A.M., Weiguny J.
Chemical Reviews,
1996
23.
Downing R.S., Kunkeler P.J., van Bekkum H.
Catalysis Today,
1997
24.
25.
Adams J.P.
Journal of the Chemical Society Perkin Transactions 1,
2002
26.
M. E. Tranquillini and G. Finizia, PCT In. Appl. WO 9425445 (Chem. Abstr., 1995, 122, 133229).
27.
A. Tomaru, T. Kaino, T. Harihara and S. Matsumoto, Japanese Patent 89-124834, 1989 (Chem. Abstr., 1990, 112, 45281).
28.
Y. Takeya, Japanese Patent 93-61082, 1993 (Chem. Abstr., 1993, 119, 149204).
29.
Nicoud J.F.
Molecular Crystals and Liquid Crystals,
1988
30.
J. F. Hartwig, S. Shashank, Q. Shen and F. Barrios-Landeros, in Patai's Chemistry of Functional Groups. Anilines, ed. Z. Rappoport, Wiley, 2009.
31.
Akhrem I.S., Avetisyan D.V., Vitt S.V., Petrovskii P.V.
Mendeleev Communications,
2005
32.
Bakke J.M., Knudsen B., Bäckvall J., Viñas C., Ayllón J.A., Paulsen G.B., Nielsen R.I., Olsen C.E., Pedersen C., Stidsen C.E.
Acta Chemica Scandinavica,
1994
33.
Brouwer D.M., Hogeveen H.
Progress in Physical Organic Chemistry,
1972
34.
Orlinkov A.V., Akhrem I.S., Vol'pin M.E.
Russian Chemical Reviews,
1991
35.
Stewart J.J.
Journal of Computational Chemistry,
1989
36.
Saluja P.P., Kebarle P.
Journal of the American Chemical Society,
1979
37.
Abboud J.-., Castaño O., Dávalos J.Z., Gomperts R.
Chemical Physics Letters,
2001
38.
Olah G.A., Prakash G.K., Saunders M.
Accounts of Chemical Research,
1983
39.
P. R. Schreiner, D. L. Severance, W. L. Jorgensen, P. v. R. Schleyer and H. F. Schaefer III, J. Am. Chem. Soc., 1995, 117, 2663.