GSC  Vol.1 No.3 , August 2011
Combination of Transition Metals-(2,4-Pentanedionate) and P2O5 as a Regioselective Catalytic System for Nitric Acid Nitration of Ar-Himachalene
ABSTRACT
A practical system of metals-(2,4-pentanedionate) (M(acac)n (M= Fe, Zn, Co and V)) and P2O5 in the pres- ence of HNO3 catalyzes regioselective nitration of ar-himachalene 1 to mono-nitro-ar-himachalene 2 in mod- erate to high yields. Under mild conditions, the selectivity of nitration of 1 to 2 is excellent compared to the classical method using the nitro-sulphuric mixture HNO3/H2SO4, both mono- and di-nitro-ar-himachalene 2 and 3 are obtained. The reaction offers a very good method for the preparation of nitro-aromatic compounds and provides a useful entry to new functionalized terpenic products.

Cite this paper
nullI. Hossini, M. Harrad, B. Boualy, M. Ali, L. Firdoussi and A. Karim, "Combination of Transition Metals-(2,4-Pentanedionate) and P2O5 as a Regioselective Catalytic System for Nitric Acid Nitration of Ar-Himachalene," Green and Sustainable Chemistry, Vol. 1 No. 3, 2011, pp. 111-115. doi: 10.4236/gsc.2011.13018.
References
[1]   P. T. Anastas and J. Warner, “Green chemistry: Theory and Practice,” Oxford University Press, New York, 1998, p. 30.

[2]   E. J. Lenardao, R. A. Freitag, M. J. Dabdoub, A. C. Ba-tista and C. C. Silveira, “Green Chemistry: The 12 Prin-ciples of Green Chemistry and It Insertion in the Teach and Research Activities,” Quimica Nova, Vol. 26, No. 1, 2003, 123-129.

[3]   G. A. Olah, R. Malhorta and S. C. Narang, “Nitration Methods and Mechanisms,” VCH, New York, 1989.

[4]   F. F. Becker and B. K. Banik, “Polycyclic Aromatic Compounds as Anticancer Agents: Synthesis and Biolog-ical Evaluation of Some Chrysene Derivatives,” Bioor-ganic & Medicinal Chemistry Letters, Vol. 50, 1998, pp. 2877-2880.

[5]   H. Zollinger, “Color Chemistry: Properties and Applica- tions of Organic Dyes,” 2nd Edition, John Wiley, New York, 1991, p. 496.

[6]   R. Meyer, J. Kohler and A. Homburg, “Explosives,” 5th Edition, Wiley, New York, 2002, p. 253. doi:10.1002/3527600515

[7]   C. K. Ingold, “Structure and Mechanism in Organic Che- mistry,” 2nd Edition, Cornell University Press, Ithaca, NY, 1969, p. 563.

[8]   G. A. Olah and S. J. Kuhnin, “Friedel-Crafts and Related Reactions,” John Wiley, New York, Vol. 3, 1964, p. 1153.

[9]   J. G. Hoggett, R. B. Moodie, J. R. Penton and K. Scho-field, “Nitration and Aromatic Reactivity,” Cambridge University Press, London, 1971, p. 757.

[10]   K. Schofield, “Aromatic Nitration”, Cambridge University Press, London, 1980, p. 368.

[11]   B. Baghernejad, M. M. Heravi, H. A. Oskooie, Y. S. Be- heshtiha, “Synthesis and Biological Evaluation of Some Chrysene Derivatives an Efficient and Regioselective Ni-tration of Phenols Using NH4NO3, KHSO4,” Gazi Uni-versity Journal of Science, Vol. 22, No. 3, 2009, pp. 169- 173.

[12]   Cornélis, A. Gerstmans, P. Laszlo, “Title of This Paper,” Chemical Letters, Vol. *, No. *, 1988, pp. 1839-1842;

[13]   B. Gigante, P. Laszlo, A. Cornélis, M. J. Marcelo-Curto, “Name of this patent,” European Patent No. 94/19310, 1994.

[14]   M. Choudary, M. Sateesh, M. Lakshmi, K. K. Rao, K. V. Ram, K. V. Raghavan and J. P. Sarma, “Selective Nitra-tion of Aromatic Compounds by Solid Acid Catalysts,” Chemical Communications, Vol. 26, No. 1, 2000, pp. 25- 26. doi:10.1039/a908011b

[15]   Gigantee, A. O. Prazeres, M. J. Marcelo-Curto, A. Cor- nelis, P. Laszlo, “Title of This Paper,” The Journal of Organic Chemistry, Vol. 60, No. *, 1995, pp. 3445-3447.

[16]   F. J. Waller, A. G. M. Barrett, D. C. Braddock, R. M. McKinnell and D. Ramprasad, “Lanthanide(III) and Group IV Metal Triflate Catalysed Electrophilic Nitration: ‘Nitrate Capture’ and the R?le of the Metal Centre,” Journal of the Chemical Society, Perkin Transactions 1, No. 8, 1999, pp. 867-871. doi:10.1039/a809914f

[17]   R. R. Bak and A. J. Smallridge, “A Fast and Mild Method for the Nitration of Aromatic Rings,” Tetrahedron Letters, Vol. 42, No. 38, 2001, pp. 6767-6769. doi:10.1016/S0040-4039(01)01378-8

[18]   H. Suzuki, S. Yonezawa, N. Nonoyama and T. Mori, “Iron(III)-Catalysed Nitration of Non-Activated and Mo- derately Activated Arenes with Nitrogen Dioxide-Mo- lecular Oxygen under Neutral Conditions,” Journal of the Chemical Society, Perkin Transactions 1, No. 19, 1996, pp. 2385-2389. doi:10.1039/p19960002385

[19]   J. H. Adrian, W. R. Millar and P. B. John, “Title of This Paper,” Sandall Org. Bio-mol. Chem., Vol. 2, No. *, 2004, pp. 90-92.

[20]   R. J. Bartelt, A. A. Cosse, B. W. Zilkowski, D. Weisleder and F. A. Momany, “Male-Specific Sesquiterpenes from Phyllotreta and Aphthona Flea Beetles,” Journal of Che- mical Ecology, Vol. 27, No. 12, 2000, pp. 2397-2423.

[21]   K. Mori, “Synthesis of (R)-ar-Turmerone and Its Con-version to (R)-ar-Himachalene, a Pheromone Component of the Flea Beetle: (R)-ar-Himachalene Is Dextrorotatory in Hexane, While Levorotatory in Chloroform,” Tetrahe-dron: Asymmetry, Vol. 16, No. 3, 2005, pp. 685-692. doi:10.1016/j.tetasy.2004.11.077

[22]   J. C. Chalchat, R. P. Garry and A. Michet, “Essential Oil in Sawdust of Cedrus Atlantica from Morocco,” JOER, Vol. 6, No. *, 1994, pp. 323-325.

[23]   R. P. Adams, “Cedar Wood Oil—Analysis and Proper- ties,” In: H. F. Linskens and J. F. Jackson, Eds., Modern Methods of Plant Analysis New Series, Vol. 12, Essential Oils and Waxes, Springer-Verlag, New York, 1991, pp. 159-173.

[24]   K. Mori, “Synthesis of Optically Active Pheromones,” Tetrahedron, Vol. 45, No. 11, 1989, pp. 3233-3298. doi:10.1016/S0040-4020(01)81007-3

[25]   R. C. Pandey and S. Dev, “Studies in Sesquiterpenes— XXX 1: Synthesis of ar-Himachalene and Himachalanes,” Tetrahedron, Vol. 24, No. 10, 1968, pp. 3829-3839 doi:10.1016/S0040-4020(01)92590-6

[26]   B. Abouhamza, S. Allaoud and A. Karim, “Title of This Paper,” Molecule, Vol. 6, No. *, 2001, pp. **-**.

[27]   A.R. Hajipour and A. E. Ruoho, “Nitric Acid in the Presence of P2O5 Supported on Silica Gel—A Useful Reagent for Nitration of Aromatic Compounds under Solvent-Free Conditions,” Tetrahedron Letters, Vol. 46, No. 48, 2005, pp. 8307-8310. doi:10.1016/j.tetlet.2005.09.178

 
 
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