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Ultrasonically Assisted Regioselective Nitration of Aromatic Compounds in Presence of Certain Group V and VI Metal Salts

¹ Department of Chemistry, Osmania University, Hyderabad, India
² Department of Chemistry, Osmania University, Hyderabad, India
³ Department of Chemistry, Osmania University, Hyderabad, India
⁴ Department of Chemistry, Osmania University, Hyderabad, India
⁵ Department of Chemistry, Osmania University, Hyderabad, India
⁶ Department of Chemistry, Osmania University, Hyderabad, India
⁷ Department of Chemistry, Osmania University, Hyderabad, India

Green and Sustainable Chemistry·Volume 02 (2012)·Pages 97–111·Published 16 August 2012·DOI10.4236/gsc.2012.23015

Abstract

Ultrasonically assisted nitration reactions (USANR) with anilides, moderately activated and non-activated aromatic compounds underwent smoothly and afforded good yields of products with high regio selectivity. Observed longer reaction times (6 - 8 hrs.) in metal catalyzed reactions reduced to (1 - 2 hrs.) under sonication. When ortho position is blocked para derivatives are obtained, and ortho nitro products are obtained when para position is blocked. In case of USANR of aromatic carbonyl and related compounds the effect of sonication is much more effective. The reactions could be completed only in few minutes.

KeywordsUltrasonically AssistedRegioselective NitrationGroup V and VI Metal SaltsReduction in Reaction Times

G. A. Olah, R. Malhotra and S. C. Narang, “Nitration: Methods and Mechanism,” VCH, New York, 1989.
C. K. Ingold, “Structure and Mechanism in Organic Chemistry,” 2nd Edition, Cornell University Press, Ithaca, 1969.
K. Schofield, “Aromatic Nitrations,” Cambridge University Press, Cambridge, 1980.
P. B. D. Dela mare and J. H. Ridd, “Aromatic Substitution, Nitration and Halogenation,” Bufferworths, London, 1959.
G. A. Olah, “Mechanism of Electrophilic Aromatic Substitutions,” Accounts of Chemical Research, Vol. 4, No. 7, 1971, pp. 240-248. doi:10.1021/ar50043a002
J. H. Ridd, “Mechanism of Aromatic Nitration,” Accounts of Chemical Research, Vol. 4, No. 7, 1971, pp. 248-253. doi:10.1021/ar50043a003
H. Fener and A. T. Nielson, “Nitro Compounds: Recent Advances in Synthesis and Chemistry,” VCH Publishers, New York, 1990.
N. C. Marziano, C. Tortato and M. Sampali, “Thermodynamic Nitration Rates of Aromatic Compounds. Part 3. Nitration of Aromatic Compounds in Concentrated Aqueous Trifluoromethanesulphonic Acid,” Journal of the Chemical Society, Perkin Transactions, Vol. 2, 1991, pp. 423-429. doi:10.1039/p29910000423
S. V. Ley and C. M. R. Low, “Ultrasound in Synthesis,” Springer, Berlin, 1989. doi:10.1007/978-3-642-74672-7
W. T. Richards and A. L. Loomi, “The Chemical Effects of High Frequency Sound Waves I. A Preliminary Survey,” Journal of the American Chemical Society, Vol. 49, No. 12, 1927, pp. 3086-3100. doi:10.1021/ja01411a015
T. J. Mason and J. P. Lorimer, “Sonochemistry: Theory, Applications and Uses of Ultrasound in Chemistry,” John Wiley and Sons, New York, 1988.
T. J. Mason, “Ultrasound in Synthetic Organic Chemistry,” Chemical Society Reviews, Vol. 26, No. 6, 1997, pp. 443-451. doi:10.1039/cs9972600443
V. Singh, K. P. Kaur, A. Khurana and G. L. Kad, “Ultra-sound: A Boon in Synthesis of Organic Compounds,” Resonance, Vol. 3, No. 9, 1998, p. 56-60.
T. J. Mason, “Chemistry with Ultrasound,” Elsevier Science Publishers Ltd., London, 1990.
T. J. Mason and D. Peters, “Practical Sonochemistry: Power Ultrasound Uses and Applications,” 2nd Edition, Hoorwood Publishing, Chichester, 2003.
K. S. Suslick, “Ultrasound: Its Chemical, Physical and Biological Effects,” VCH, New York, 1988.

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Ultrasonically Assisted Regioselective Nitration of Aromatic Compounds in Presence of Certain Group V and VI Metal Salts

Abstract

References (31)