An efficient and selective method for conversion of oximes, semicarbazones and phenylhydrazones to the corresponding carbonyl compounds under solvent-free conditions

Document Type : Articles


1 Young Researchers and Elite Club, Aliabad Katoul Branch, Islamic Azad University, Aliabad Katoul, Iran.

2 Department of Chemistry, Mazandaran University, Babolsar, Iran.


o-Xylylenebis (triphenylphosphonium peroxymonosulfate) (1) was easily prepared from an aqueous solution of oxone and o-xylylenebis- (triphenylphosphonium bromide). This Compound (1) is a useful and selective reagent for conversion of oximes, semicarbazones and phenylhydrazones to the corresponding carbonyl compounds. The reaction was carried out under solvent-free conditions and in the presence of catalytic amount of aluminium chloride. This method shows a good selectivity in oxidation of oximes, semicarbazones and phenylhydrazones in the presence of aliphatic and aromatic alcohols. The advantages of the present method include good functional group tolerance, high yields of products, simple experimental procedure and purification, no solvent and short reaction times.


[1] T.W. Greene, P.G.M. Wuts, Protective Groups in Organic Synthsis; John Wiley & sons, New York, (1991).
[2] (a) R.S. Varma, H.M. Meshram, Tetrahedron Lett. 38 (1997) 7973-7976. (b) B.M. Khadilkar, P.M. Bendale, Tetrahedron Lett. 39 (1998) 5867-5868. (c)  M. Hakimi, N. Feizi, H. Hassani, H. Vahedi, P.S. Thomas. Synth. Commun. 40 (2010) 725-731. (d) M. Curini, O. Rosati E.U. Pisani, Costantino, Synlett 4 (1996) 333-334. (e) G.S. Zhang, H. Gong, Synth. Commun. 29 (1999) 2591-2596. (f) M.M. Lakouraj, M. Noorian, M. Mokhtary, React. Func. Polym. 66 (2006) 910-915.
[3] E.B.J. Hershberg, J. Org. Chem. 13 (1948) 542-546.
[4] (a) P. Laszlo, E. Polla, Synthesis, (1985) 439-440. (b) D.S. Bose, A.V. Narsaiah, V. Lakshminarayana, Synth. Commun. 30 (2000) 3112-3125. (c) N.C. Ganguly, S. Nayek, S.K. Barik. Synth. Commun. 39 (2009) 4053-4061. (d)  L. Saikia, S. Das, A.J. Thakur. Synth. Commun. 41 (2011) 1071-1076. (e) A. Boruah, B. Baruah, D. Prajapati, J.S. Sandhu, Synlett, 11 (1997) 1251-1253. (f) G.A. Olah, Q. Liao, C.S. Lee, G.K.Surya Prakash, Synlett 5 (1993) 427-429. (g) R. Hosseinzadeh, M. Tajbakhsh M.Y. Niaki, Tetrahedron Lett. 43 (2002) 9413-9416. (h) M. Tajbakhsh, I.M. Baltork F.R. Lahmali, J. Chem. Res. (2003) 710-711.
[5] (a) R. Hosseinzadeh, M. Tajbakhsh, Z. Lasemi, A. Sharifi, Bull. Korean Chem. Soc. 25 (2004) 1143-1146. (b) R.J. Giguere, T.L. Bray, S.M Duncan, G. Majetich, Tetrahedron Lett. 27 (1986) 4945-4948. (c) K. Smith, Ed.; Solid Supports and Catalysts in Organic Synthesis, Prentice Hall, New York, (1992). (d) R.A. Abramovitch, D.A. Abramovitch, K. Iyanar, K. Tamareselvy, Tetrahedron Lett. 32 (1991) 5251. (e) P. Michale, D. Migos, R. Baghurst, Chem. Soc. Rev. 20 (1991) 1-47. (f) R.S. Varma, A.K. Chatterjee, M. Varma, Tetrahedron Lett. 34 (1993) 3207-3210. (g) R.S. Varma, R. Dahiya, R.K. Saini, Tetrahedron Lett. 38 (1997) 7823-7824. (h) S.S. Deshpande, S.U. Sonavane, R.V. Jayaram, Catalysis Comminucations 9 (2006) 639-644. (f) A.R. Hajipour, S.E. Mallakpour, J. Chem. Lett. 29 (2000) 460-461.
[6] (a) S.S. Deshpande, S.U. Sonavane, R.V. Jayaram, Catal. Commin. (2006) 9 639-644. (b) M.M. Heravi, L. Ranjbar, F. Derikvand, H.A. Oskooie, F.F. Bamoharram, J. Molecular Catal. A: Chem. 265 (2007) 186-188. (c) R. Hosseinzadeh, M. Tajbakhsh, A. Shakoori, M.Y. Niaki, Monatsh. Chem. 135 (2004) 1243-1249. (d) M.M. Mojtahedi, M. Javadpour, M.S. Abaee, Ultrason. Sonochem. 15 (2008) 828-832. (e) M. Tajbakhsh, I. M. Baltork, F.R. Lahmali, Phosphorus, Sulfur, Silicon Relat. Elem. (2003) 178 2617-2620. (g) M. Tajbakhsh, I.M. Baltork, S.K. Alimohammadi, Monatsh. Chem. 134 (2003) 1571-1575.
[7] C.E. Griffin, K.R. Martim, B.E. Douglas, J. Org. Chem. 27 (1962) 1627.
[8] (a) M. Tajbakhsh, M.M. Lakouraj, Kh. Yadollahzadeh, Phosphorus, Sulfur, Silicon Relat. Elem. 180 (2005) 2431-2437. (b) M. Tajbakhsh, M.M. Lakouraj, Kh. Yadollahzadeh. J. Chem. Res. (2005) 766-769.
[9] J. Mluchowski, Chem. Papers 52 (1998) 45-51.
[10] (a) I.M. Baltork, Sh. Pourshirvani, Synth. Commun.
26 (1996) 1-7. (b) B.P. Bandgar, B. Kunde, J.L.
Thote, Synth. Commun. 27 (1997) 1149-1152. (c) M. Tajbakhsh, R. Hosseinzadeh, M.S. Shahabi, J. Chin. Chem. Soc. 52 (2005) 1005-1009. (d) G.S. Zhang,
B. Chai, Synth. Commun. (2000) 30 2507-2513. (e) D.S. Bose, A.V. Narasaiah, Synth. Commun. 30 (2000)
1153-1157. (f) G.S. Zhang, D.H. Yang, M.R. Chen, K. Cai, Synth. Commun. 28 (1998) 607-611. (g) N.C. Ganguly, A.K. Sukai, D. Sripada, D.Prithwirj, Synth. Commun. 31 (2001) 1607-1612. (h) Y.F. Zhou, F. Lin, X. L. Lu, Ch. Zhang, Q. Wang, X.N. Zou, J.D. Lou, Oxid. Commun. 35 (2012) 45–50. (i) A. Khazaei, S. Mallakpour, R.G. Vaghei, Iran. Polym. J. 12 (2003) 115-118. (j) F.P. Ballistreri, U. Chiacchio, A. Rescifina, G. Tomaselli, R. M. Toscano, Molecules 13 (2008) 1230-1237.