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Copyright (c) 2014 Khadijah M. Al-Zaydi
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A View of an Unusual Route for Certain Phosphorus Ylide
Corresponding Author(s) : Khadijah M. Al-Zaydi
Asian Journal of Chemistry,
Vol. 26 No. 23 (2014)
Abstract
An abnormal route for the synthesis of (5-(2-(2-cyanophenyl)hydrazono)-2,3-bis(methoxycarbonyl)-4-phenylcyclopent-2-enyl)triphenyl phosphonium (5) has been patented. The synthesis of compound (5) was performed by the reaction of 2-(2-(1,3-dioxo-1-phenylpropan-2-ylidene)hydrazinyl)benzonitrile with dimethylacetylene dicarboxylate in dichloromethane at room temperature for 2 h in order to yield a cyclic intermediate. The subsequent addition of triphenylphosphine afforded the desired product as interesting crystals suitable for X-ray crystallographic analysis. The synthesized compound was characterized based on (FT-IR, NMR, elemental analysis and single crystal X-ray diffraction studies). A possible mechanism for the synthesis was also reported.
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- K.M. Al-Zaydi, Method for Making Phosphorus Yilide, US Patent 8,278,477 B2, October 2 (2012).
- D.E.C. Cobridge, Phosphorus: An Outline of the Chemistry, Biochemistry and Uses, Elsevier, Amsterdam, edn 5 (1955).
- R. Engel, Synthesis of Carbon-Phosphorus Bonds, CRC Press: Boca Raton (1988).
- J.I.G. Cadogan, Organophosphorus Reagents in Organic Synthesis, Academic Press: New York (1979).
- A.W. Johnson, Ylides and Imines of Phosphorus, Wiley, New York (1993).
- A.W. Johnson, Ylide Chemistry, Academic Press, New York (1966).
- E. Zbiral, Synthesis, 775 (1974).
- K.B. Becker, Tetrahedron, 36, 1717 (1980).
- P. Ferrer, C. Avendaño and M. Söllhuber, Liebigs Ann. Chem., 1995, 1895 (1995).
- O.I. Kolodiazhnyi, Russ. Chem. Rev., 66, 225 (1997).
- H.J. Bestmann and O. Vostrowsky, Top. Curr. Chem., 109, 85 (1983).
- H.J. Bestmann and R. Zimmermann, Top. Curr. Chem., 20, 1 (1971).
- M. Zakarianejad, H. Ghasempour, S.M. Habibi-Khorassani, M.T. Maghsoodlou, B. Makiabadi, M. Nassiri, Z. Ghahghayi and A. Abedi, ARKIVOC, 171 (2013).
- Y.-T. Lee, Jang, Syu, Chou, Lee and Lin, Chem. Commun., 48, 8135 (2012).
- R. Azhakar, S.P. Sarish, H.W. Roesky, J. Hey and D. Stalke, Organometallics, 30, 2897 (2011).
- D.R. Gautam, K.E. Litinas, K.C. Fylaktakidou and D.N. Nicolaides, Phosphorus Sulfur Silicon Relat. Elem., 178, 1851 (2003).
- M.K. Gurjar, R.D. Wakharkar, G.R. Desiraju, A. Nangia, J.S. Yadav, A.C. Burman, R. Mukherjee, H.B.R. Borate, S. Chandrasekhar, M. Jaggi, A.T. Singh, K. Kapoor, S. Sarkhel and K.V.V.M. Sairam, US Patent 7,179,937 (2007).
- J.L. Methot and W.R. Roush, Adv. Synth. Catal., 346, 1035 (2004).
- K.M. Al-Zaydi, J. Saudi Chem. Soc., 6, 477 (2002).
- K.M. Al-Zaydi, Heterocycles, 78, 2003 (2009).
- K.M. Al-Zaydi, Ultrason. Sonochem., 16, 805 (2009).
- K.M. Al-Zaydi, R.M. Borik and M.H. Elnagdi, Molecules, 8, 910 (2003).
- Al-Zaydi and R.M. Borik, Molecules, 12, 2061 (2007).
- K.M. Al-Zaydi, E.A. Hafez and M.H. Elnagdi, J. Chem. Res., 154, 0510 (2000).
- Crystallographic data for compounds (5) and (6) reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications CCDC 698609, 698616 respectively these data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK; Fax: +44 1223 336033; E-mail: deposit@ccdc.cam.ac.uk).
- M. Freytag, S. Ito and M. Yoshifuji, Chem. Asian J., 1, 693 (2006).
- K.M. Al-Zaydi, R.M. Borik and M.H. Elnagdi, Ultrason. Sonochem., 16, 660 (2009).
References
K.M. Al-Zaydi, Method for Making Phosphorus Yilide, US Patent 8,278,477 B2, October 2 (2012).
D.E.C. Cobridge, Phosphorus: An Outline of the Chemistry, Biochemistry and Uses, Elsevier, Amsterdam, edn 5 (1955).
R. Engel, Synthesis of Carbon-Phosphorus Bonds, CRC Press: Boca Raton (1988).
J.I.G. Cadogan, Organophosphorus Reagents in Organic Synthesis, Academic Press: New York (1979).
A.W. Johnson, Ylides and Imines of Phosphorus, Wiley, New York (1993).
A.W. Johnson, Ylide Chemistry, Academic Press, New York (1966).
E. Zbiral, Synthesis, 775 (1974).
K.B. Becker, Tetrahedron, 36, 1717 (1980).
P. Ferrer, C. Avendaño and M. Söllhuber, Liebigs Ann. Chem., 1995, 1895 (1995).
O.I. Kolodiazhnyi, Russ. Chem. Rev., 66, 225 (1997).
H.J. Bestmann and O. Vostrowsky, Top. Curr. Chem., 109, 85 (1983).
H.J. Bestmann and R. Zimmermann, Top. Curr. Chem., 20, 1 (1971).
M. Zakarianejad, H. Ghasempour, S.M. Habibi-Khorassani, M.T. Maghsoodlou, B. Makiabadi, M. Nassiri, Z. Ghahghayi and A. Abedi, ARKIVOC, 171 (2013).
Y.-T. Lee, Jang, Syu, Chou, Lee and Lin, Chem. Commun., 48, 8135 (2012).
R. Azhakar, S.P. Sarish, H.W. Roesky, J. Hey and D. Stalke, Organometallics, 30, 2897 (2011).
D.R. Gautam, K.E. Litinas, K.C. Fylaktakidou and D.N. Nicolaides, Phosphorus Sulfur Silicon Relat. Elem., 178, 1851 (2003).
M.K. Gurjar, R.D. Wakharkar, G.R. Desiraju, A. Nangia, J.S. Yadav, A.C. Burman, R. Mukherjee, H.B.R. Borate, S. Chandrasekhar, M. Jaggi, A.T. Singh, K. Kapoor, S. Sarkhel and K.V.V.M. Sairam, US Patent 7,179,937 (2007).
J.L. Methot and W.R. Roush, Adv. Synth. Catal., 346, 1035 (2004).
K.M. Al-Zaydi, J. Saudi Chem. Soc., 6, 477 (2002).
K.M. Al-Zaydi, Heterocycles, 78, 2003 (2009).
K.M. Al-Zaydi, Ultrason. Sonochem., 16, 805 (2009).
K.M. Al-Zaydi, R.M. Borik and M.H. Elnagdi, Molecules, 8, 910 (2003).
Al-Zaydi and R.M. Borik, Molecules, 12, 2061 (2007).
K.M. Al-Zaydi, E.A. Hafez and M.H. Elnagdi, J. Chem. Res., 154, 0510 (2000).
Crystallographic data for compounds (5) and (6) reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications CCDC 698609, 698616 respectively these data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK; Fax: +44 1223 336033; E-mail: deposit@ccdc.cam.ac.uk).
M. Freytag, S. Ito and M. Yoshifuji, Chem. Asian J., 1, 693 (2006).
K.M. Al-Zaydi, R.M. Borik and M.H. Elnagdi, Ultrason. Sonochem., 16, 660 (2009).