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Poly(ethylene glycol) Supported Metal Nitrates as Well-Organized Reagents for Hunsdiecker Conversion of α,β-Unsaturated Acids to β-Nitrostyrenes under Solvent and Acid-Free Conditions
Corresponding Author(s) : K.C. Rajanna
Asian Journal of Chemistry,
Vol. 31 No. 8 (2019): Vol 31 Issue 8
Abstract
Poly(ethylene glycol) (PEG) supported metal nitrates such as ferric nitrate and manganese nitrate were accomplished as well-organized reagents for Hunsdiecker conversion of α,β-unsaturated acids to β-nitrostyrenes under acid-free and solvent free conditions using grind-stone technique. However, in the case of unsaturated aliphatic acids, nitro alkene derivatives were obtained as products. PEG-400 was found the best among the other PEGs (PEG-200,300, 400, 600, 3000 and 6000) used in this protocol.
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- P. Anastas and J. Warner, Green Chemistry: Theory and Practice, Oxford University Press: New York (1998).
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References
P. Anastas and J. Warner, Green Chemistry: Theory and Practice, Oxford University Press: New York (1998).
L.E. Kaïm, L. Gautier, L. Grimaud, L.M. Harwood and V. Michaut, Green Chem., 5, 477 (2003); https://doi.org/10.1039/B306242B.
G.R. Desiraju and B.S. Goud, ed.: V.V. Boldyrev, Reactivity of Solids: Present, Past and Future, Blackwell Sciences: London, p. 223 (1995).
K. Tanaka and F. Toda, Chem. Rev., 100, 1025 (2000); https://doi.org/10.1021/cr940089p.
G.W.V. Cave, C.L. Raston and J.L. Scott, Chem. Commun., 2159 (2001); https://doi.org/10.1039/b106677n.
I. Mohammadpoor-Baltork, M. Sadeghi and A.-H. Adibi, Molecules, 6, 900 (2001); https://doi.org/10.3390/61100900.
J.D. Lou and Z.N. Xu, Tetrahedron Lett., 43, 6095 (2002); https://doi.org/10.1016/S0040-4039(02)01333-3.
J.D. Lou and Z.N. Xu, Tetrahedron Lett., 43, 8843 (2002); https://doi.org/10.1016/S0040-4039(02)02234-7.
J.D. Lou and Z.N. Xu, Tetrahedron Lett., 43, 6149 (2002); https://doi.org/10.1016/S0040-4039(02)01345-X.
J.L. Scott, D.R. MacFarlane, C.L. Raston and M. Teoh, Green Chem., 2, 123 (2000); https://doi.org/10.1039/b000825g.
C.L. Raston and J.L. Scott, Green Chem., 2, 49 (2000); https://doi.org/10.1039/a907688c.
M.M. Ali, K.C. Rajanna and P.K. Sai Prakash, Synlett, 2001, 251 (2001); https://doi.org/10.1055/s-2001-10765.
M.M. Ali, S. Sana, Tasneem, K.C. Rajanna and P.K. Saiprakash, Synth. Commun., 32, 1351 (2002); https://doi.org/10.1081/SCC-120003631.
K.C. Rajanna, M. Moazzam Ali, S. Sana, Tasneem and P.K. Saiprakash, J. Dispers. Sci. Technol., 25, 17 (2004); https://doi.org/10.1081/DIS-120027663.
K.C. Rajanna, M.M. Ali, S. Sana and P.K. Saiprakash, Chem. Lett., 1, 48 (2000).
C. Hunsdiecker and H. Hunsdiecker, Ber. Dtsch. Chem. Ges., 75, 291 (1942); https://doi.org/10.1002/cber.19420750309.
R.G. Johnson and R.K. Ingham, Chem. Rev., 56, 219 (1956); https://doi.org/10.1021/cr50008a002.
A.G. Smith, Organic Synthesis, Wiley Interscience: New York (1993).
S. Ramgopal, K. Ramesh, A. Chakradhar, N.M. Reddy and K.C. Rajanna, Tetrahedron Lett., 48, 4043 (2007); https://doi.org/10.1016/j.tetlet.2007.04.026.
K.C. Rajanna, K. Ramesh, S. Ramgopal, S. Shylaja, P.G. Reddy and P.K. Saiprakash, Green. Sustain. Chem., 1, 132 (2011); https://doi.org/10.4236/gsc.2011.14022.
T.J. Dickerson, N.N. Reed and K.D. Janda, Chem. Rev., 102, 3325 (2002); https://doi.org/10.1021/cr010335e.
B. Das, V.S. Reddy and M. Krishnaiah, Tetrahedron Lett., 47, 8471 (2006); https://doi.org/10.1016/j.tetlet.2006.09.153.
S. Chandrasekhar, N.R. Reddy, S.S. Sultana, Ch. Narsihmulu and K.V. Reddy, Tetrahedron, 62, 338 (2006); https://doi.org/10.1016/j.tet.2005.09.122.
J.-H. Li, X.-C. Hu, Y. Liang and Y.-X. Xie, Tetrahedron, 62, 31 (2006); https://doi.org/10.1016/j.tet.2005.09.138.
S. Chandrasekhar, C. Narsihmulu, B. Saritha and S.S. Sultana, Tetrahedron Lett., 45, 5865 (2004); https://doi.org/10.1016/j.tetlet.2004.05.153.f
B. Das, M. Krishnaiah, P. Thirupathi and K. Laxminarayana, Tetrahedron Lett., 48, 4263 (2007); https://doi.org/10.1016/j.tetlet.2007.04.062.
A.I. Vogel, Text Book of Practical Organic Chemistry, Longman: London and New York, edn 4 (1986).