Kinetics and Mechanism of the Formation of Ylides, 1, 4 or 1, 5-Diionic Organophosphorus and Phosphonate Esters: A Review

Author(s): Sayyed Mostafa Habibi-Khorassani*, Mehdi Shahraki, Bahareh Mostafa.

Journal Name: Mini-Reviews in Organic Chemistry

Volume 16 , Issue 1 , 2019

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Graphical Abstract:


Abstract:

The kinetics and mechanism of the formation of some ylides,1,4 or 1,5-diionic organophosphorus and phosphonate esters have been reviewed. The UV-vis spectrophotometry, stopped-flow and variable-temperature 1H-NMR spectroscopy along with the theoretical calculations were used as investigative techniques.

Keywords: NMR techniques, kinetics, mechanism, ylides, phosphonate esters, diionic organophosphorus.

[1]
Wittig, G. From diyls to ylides to my idyll. Science, 1980, 210, 600-604.
[2]
Laszlo, P. Organic Reactions, Simplicity and Logic and Simplicity.John Wiley & Son Ltd.: New York, ; , 1995.
[3]
Corbridge, D.E.C. Phosphorus: An Outline of its Chemistry, Biochemistry and Technology; Elsevier Scientific Publishing Company: Amsterdam, 1985.
[4]
Murphy, P.J. Organophosphorus Reagents A Pract. Approach in Chemistry; Oxford University Press: Oxford, 2004.
[5]
Engel, R. Synthesis of Carbon - Phosphorus Bonds; CRC Press: Florida, 2004.
[6]
Cadogan, J.I.G. Organophosphorus reagents in organic synthesis; Academic Press: Cambridge, 1979.
[7]
Engel, R. Synthesis of Carbon-Phosphorus Bonds; CRC Press: Florida, 1988.
[8]
Hudson, H.R. Nucleophilic Reactions of Phosphines.The Chemistry of Organophosphorus Compounds, Primary, Secondary, and Tertiary Phosphates and Heterocyclic Organophosphorus III Compounds; Hartley, F.R., Ed.; Wiley: New York, 1990.
[9]
Cobridge, D.E.C. Phosphorus: An Outline of Chemistry, Biochemistry and Uses; Verlag Elsevier Scientific Publishing Company: Amsterdam, 1995.
[10]
Johnson, A.W. Aromaticity in macrcyclic polypyrrolic ring system. Pure Appl. Chem., 1971, 28, 195-218.
[11]
Johnson, A.W. Ylid Chemistry; Academic Press: Cambridge, 1966.
[12]
Kolodiazhnyi, O.I. Phosphorus ylides; Wiley: New York, 1999.
[13]
Hudson, H.R. Acid-Base and Hydrogen-Bonding Properties of Phosphines.The Chemistry of Organophosphorus Compounds, Primary, Secondary, and Tertiary Phosphates and Heterocyclic Organophosphorus III Compounds; Hartley, F.R., Ed.; Wiley: New York, 1990.
[14]
Maryanoff, B.E.; Reitz, A.B. The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects. Chem. Rev., 1989, 89(4), 863-927.
[15]
Shen, Y.; Ni, J. A novel sequential transformations of phosphonate. Highly stereoselective synthesis of perfluoroalkylated α-fluoro-α, β unsaturated esters. J. Org. Chem., 1997, 62(21), 7260-7262.
[16]
Islami, M.R.; Mollazehi, F.; Badiei, A.; Sheibani, H. Serendipitous synthesis of 1, 4-benzothiazin derivatives using 2-[(2-aminophenyl) disulfanyl] aniline. ARKIVOC, 2005, 15, 25-29.
[17]
Pietrusiewicz, K.M.; Zablocka, M. Preparation of scalemic P-chiral phosphines and their derivatives. Chem. Rev., 1994, 94(5), 1375-1411.
[18]
Shen, Y. New synthetic methodologies for carbon-carbon double bond formation. Acc. Chem. Res., 1998, 31(9), 584-592.
[19]
Gilchrist, T.L. Heterocyclic Chemistry; Wiley: New York, 1985.
[20]
Yavari, I.; Anary-Abbasinejad, M.; Alizadeh, A. A novel approach to the synthesis of highly functionalized furans. Tetrahedron Lett., 2002, 43(25), 4503-4505.
[21]
Yavari, I.; Adib, M.; Hojabri, L. Vinyltriphenylphosphonium salt mediated serendipitous synthesis of aryliminophosphoranes. Tetrahedron, 2002, 58(36), 7213-7219.
[22]
Kaniskan, N.; Elmali, D.; Civcir, P.U. Synthesis and characterization of novel heterosubstituted pyrroles, thiophenes, and furans. ARKIVOC, 2008, 2008(xii), 17-29.
[23]
Yavari, I.; Adib, M.; Jahani-Mogaddam, F.; Sayahi, M.H. A simple synthesis of stable heterocyclic phosphorus ylides derived from NH-acids. Phosphorus Sulfur Silicon Relat. Elem., 2002, 177(3), 545-553.
[24]
Ramazani, A.; Joo, S.W.; Nasrabadi, F.Z. Environmentally green synthesis of thioformamide derivatives. Turk. J. Chem., 2013, 37(3), 405-412.
[25]
Maghsoodlou, R.M.T.; Habibi-Khorassani, S.M. Stereoselective synthesis of pyrrole phosphonate esters from the reaction of triphenylphosphite and dimethyl acetylenedicarboxylate in the presence of pyrrole in aqueous solution. J. Chem. Res., 2006, 6, 364-365.
[26]
Maghsoodlou, M.T.; Rostami Charati, F.; Habibi Khorassani, S.M.; Khosroshahrodi, M.; Makha, M. Synthesis of Pyrrole phosphonate esters : Emphasis on pyrrole NH acids and dialkylacetylenic esters substitution. Iran J. Chem. Chem. Eng., 2008, 27(1), 105-113.
[27]
Maghsoodlou, M.T.; Heydari, R.; Hazeri, N.; Habibi-Khorassani, S.M.; Nassiri, M.; Ghasemzadeh, M.; Salehzadeh, J.; Gharechaei, Z. Synthesis of aromatic amine phosphonato ester derivatives from the stereoselective reaction between triphenyl phosphite and dimethyl acetylenedicarboxylate in the presence of derivatives of aromatic amines. Heteroatom Chem., 2009, 20(4), 240-245.
[28]
Maghsoodlou, M.T.; Hazeri, N.; Habibi-Khorassani, S.M.; Heydari, R.; Marandi, G.; Lashkari, M.; Bagherpour, K.; Gharechaei, Z. Synthesis of phosphonato esters involving heterocyclic biological bases in a highly diastereoselective and chemoselective route. Monatsh. Chem., 2010, 141(3), 351-356.
[29]
Yavari, I.; Alizadeh, A.; Anary-Abbasinejad, M. Reaction between heterocyclic NH-acids and dibenzoylacetylene in the presence of triphenylphosphine. Simple synthesis of 1-(3-furyl)-1H-imidazole derivatives. Tetrahedron Lett., 2002, 43(51), 9449-9452.
[30]
Yavari, I.; Bayat, M. Triphenylphosphine-catalyzed simple synthesis of vinyl-substituted saccharins. Phosphorus Sulfur Silicon Relat. Elem., 2002, 177(11), 2537-2545.
[31]
Islami, M.R.; Gharib-Hosseini, S.; Bijanzadeh, H.R. Preparation of 1, 4-benzothiazines using stable phosphorus ylides. Phosphorus Sulfur Silicon Relat. Elem., 2007, 182(12), 2949-2953.
[32]
Aminkhani, A.; Kabiri, R.; Habibi-Khorassani, S.M.; Heydari, R.; Maghsoodlou, M.T.; Marandi, G.; Lashkari, M.; Rostamizadeh, M. Synthesis of heterocyclic phosphonato esters by reaction between triphenyl phosphite and acetylenic diesters in the presence of sulfur-containing heterocyclic compounds. J. Sulfur Chem., 2009, 30(5), 500-506.
[33]
Habibi-khorassani, S.M.; Maghsoodlou, M.T.; Shahraki, M.; Talaiefar, S.; Aboonajmi, J. Kinetic and mechanistic investigation of pyrano [2, 3-d] pyrimidine formation in the presence of catalyst under novel one-pot three-component reaction. Org. Chem. Int., 2014, 2014, 1-11.
[34]
Maghsoodlou, M.T.; Hazeri, N.; Khorassani, S.M.H.; Heydari, R.; Nassiri, M.; Marandi, G.; Moeeni, Z.; Niromand, U.; Torbaghan, Z.E. An efficient synthesis of stable phosphorus ylides derived from triphenylphosphine, dialkyl acetylenedicarboxylates, and an NH-acid. Phosphorus Sulfur Silicon Relat. Elem., 2006, 181(4), 865-877.
[35]
Khorassani, S.M.; Maghsoodlou, M.T.; Ebrahimi, A.; Roohi, H.; Zakarianezhad, M.; Moradian, M. Kinetic investigation of the reactions between triphenylphosphine, dialkyl acetylenedicarboxy-lates and SH-acid such as 2-thiazoline-2-thiol or 2-mercapto-benzoxazole by UV spectrophotometry. Prog. React. Kinet. Mech., 2005, 30(1-2), 127-143.
[36]
Khorassani, S.M.H.; Maghsoodlou, M.T.; Ebrahimi, A.; Roohi, H.; Zakarianezhad, M.; Dasmeh, H.R.; Moradian, M. Kinetic investigation of the reaction between triphenylphosphine, dialkyl acetylenedicarboxylate, and carbazole by the UV spectrophotometry technique. Phosphorus Sulfur Silicon Relat. Elem., 2006, 181(5), 1103-1115.
[37]
HabibiKhorassani S.M.; Maghsoodlou, M.T.; Nassiri, M.; Zakarianezhad, M.; Fattahi, M. Synthesis of stable phosphorus ylides from 3, 5-dimethylpyrazole and kinetic investigation of the reactions by UV spectrophotometry. ARKIVOC, 2006, 16, 168-184.
[38]
Khorassani, S.M.H.; Maghsoodlou, M.T.; Ebrahimi, A.; Moradian, M.; Zakarianezhad, M. Spectrophotometric kinetic studies of the reaction between triphenylphosphine, dialkyl acetylenedicarboxy-lates and NH-acids. Asian J. Chem., 2007, 19(2), 1075.
[39]
Khorassani, S.M.H.; Maghsoodlou, M.T.; Ebrahimi, A.; Mohammadzadeh, P.; Zakarianezhad, M.; Fattahi, M. Kinetic investigation of the reactions between triphenylphosphine, dialkyl acetylenedicarboxilates and NH-acid, such as 5, 6-dimethyl benzimidazole by the UV spectrophotometry technique. Sci. Iran., 2007, 14(2), 133-141.
[40]
Khorassani, S.M.; Maghsoodlou, M.T.; Ebrahimi, A.; Roohi, H.; Zakarianezhad, M. Kinetic investigation of the reactions between triphenylphosphine, dialkyl acetylenedicarboxylates and NH-acid such as 7-azaindole by the UV spectrophotometry. Indian J. Chem., 2007, 46(5), 783-788.
[41]
Habibi Khorassani, S.M.; Maghsoodlou, M.T.; Ebrahimi, A.; Zakarianejad, M.; Fattahi, M. Kinetics and mechanism of the reactions between triphenylphosphine, dialkyl acetylenedi-carboxilates and a NH-acid, pyrazole, by UV spectrophotometry. J. Solution Chem., 2007, 36(9), 1117-1127.
[42]
Zakarianezhad, M.; Habibi-Khorassani, S.M.; Maghsoodlou, M.T.; Ghasempour, H.; Makiabadi, B. Mechanism investigation of the reaction between triphenylphosphine, dialkyl acetylene-dicarboxylates and 2-hydroxybenzimidazole: Experimental and theoretical study. Arab. J. Chem., 2012, 10(1), S814-S824.
[43]
Kazemian, M.A.; Nassiri, M.; Ebrahimi, A.; Maghsoodlou, M.T.; Habibi-Khorassani, S.M.; Vasheghani-Farahani, F. A facile synthesis, dynamic 1H NMR, and theoretical study of novel stable heterocyclic phosphorus ylides containing a tetrazole ring. ARKIVOC, 2008, 17, 173-183.
[44]
Khorassani, S.M.H.; Maghsoodlou, M.T.; Ebrahimi, A.; Zakarianezhad, M.; Mohamadzadeh, P.; Shahraki, M. Kinetic study and mechanism investigation of the reactions between triphenylphosphine, dialkyl acetylene dicarboxylates and NH-acid such as Harman. Orient. J. Chem., 2008, 24(1), 73-82.
[45]
Amin, M.; Karimi, P. Theoretical study, kinetics and mechanism investigation of the reactions between triphenylphosphine, dialkyl acetylenedicarboxilates and NH-acid such as 2-ethylimidazole by UV. Mat. Sci. Res. India, 2008, 5(2), 235-250.
[46]
Habibi-Khorassani, S.M.; Maghsoodlou, M.T.; Nassiri, M.; Kazemian, M.A.; Karimi, P. others. A facile synthesis of stable phosphorus ylides derived from 3, 6-dibromocarbazole and kinetic investigation of the reactions by UV spectrophotometry technique. Heteroatom Chem., 2008, 19(7), 723-732.
[47]
Habibi-Khorassani, M.; Maghsoodlou, M.T.; Ebrahimi, A.; Kazemian, M.A.; Zakarianejad, M. Chemoselective Synthesis of stable phosphorus ylides from 6-azauracil and mechanistic investigation of the reaction by UV spectrophotometry. Phosphorus Sulfur Silicon Relat. Elem., 2009, 184(11), 2959-2979.
[48]
Habibi-Khorassani, S.M.; Ebrahimi, A.; Maghsoodlou, M.T.; Saravani, H.; Zakarianezhad, M.; Ghahramaninezhat, M.; Kazemian, M.A.; Nassiri, M.; Khajehali, Z. Theoretical study, an efficient synthesis route to, and kinetic investigation of, stable phosphorus ylides derived from benzamide. Prog. React. Kinet. Mech., 2009, 34(3), 261-288.
[49]
Kazemian, M.A.; Karimi, P.; Habibi-Khorassani, S.M.; Ebrahimi, A.; Maghsoodlou, M.T.; Milani, F.J. Synthesis of stable phosphorus ylides from 6-chloro-2-benzoxazolinone and kinetic investigation of the reactions by UV spectrophotometry. Prog. React. Kinet. Mech., 2009, 34(1), 77-96.
[50]
Moradian, M.; Khorassani, S.M.H.; Maghsoodlou, M.T.; Ebrahimi, A.; Zakarianezhad, M.; Karimi, P. Kinetic and mechanism investigation of the reactions of triphenylphosphine, dialkyl acetylenedicarboxylates and NH-acids by Ultra Violet. Asian J. Chem., 2009, 21(2), 1069-1080.
[51]
Habibi-Khorassani, S.M.; Ebrahimi, A.; Maghsoodlou, M.T.; Charati, F.R.; Kazemian, M.A.; Karimi, P. A facile synthesis and theoretical study of novel stable heterocyclic phosphorus ylides containing a 2, 4-dimethyl-3-acetyl moiety. Phosphorus Sulfur Silicon Relat. Elem., 2010, 185(3), 559-566.
[52]
Zakarianezhad, M.; Maghsoodlou, M.T.; Makiabadi, B.; Ghasempour, H. Understanding the mechanism of stable phosphorus ylides derived from maleimide : A kinetic study. Iran J. Sci. Technol., 2012, 36(3), 251-258.
[53]
Kazemian, M.A.; Habibi-Khorassani, S.M.; Ebrahimi, A.; Maghsoodlou, M.T.; Jahani, P.M.; Ghahramaninezhad, M. A joint experimental and theoretical investigation of kinetics and mechanistic study in a synthesis reaction between triphenylphosphine and dialkyl acetylenedicarboxylates in the presence of benzhydrazide. J. Mol. Model., 2012, 18(12), 5075-5088.
[54]
International, A.; Free, O.; Reviewed, P. Understanding the mechanism of stable phosphorus ylides derived from imidazole, 2-methylimidazole or 4-methylimidazole : A Kinetic Study. Orient. J. Chem., 2012, 12(3), 1259-1269.
[55]
Zakarianejad, M.; Habibi-Khorassani, S.; Makiabadi, B.; Taheri, A. Structural effects of different NH-acids and dialkyl acetylenedicarboxylates on the kinetic parameters of stable phosphorus ylids: A mechanistic investigation. Curr. Chem. Lett., 2013, 2(2), 93-104.
[56]
Khorassani, S.M.H.; Ebrahimi, A.; Maghsoodlou, M.T.; Moradian, M.; Kazemian, M.A.; Karimi, P. Theoretical, kinetics and mechanism investigation of the reaction between triphenyl-phosphine, di-tert-butyl acetylenedicarboxilate and OH-acid. Chin. J. Chem., 2009, 3, 178-188.
[57]
Yavari, I.; Baharfar, R. Vinyltriphenylphosphonium salt mediated one-pot synthesis of functionalized 3-(triphenylphosphoranylidene) butyrolactones. Tetrahedron Lett., 1997, 38(24), 4259-4262.
[58]
Habibi-Khorassani, S.M.; Ebrahimi, A.; Maghsoodlou, M.; Asheri, O.; Shahraki, M.; Akbarzadeh, N.; Ghalandarzehi, Y. Kinetic and mechanistic insights into the pathway leading to cyclic crystalline Phosphorus ylide formation in the presence of 3-chloropentane-2, 4-dione: Theoretical and stopped-flow approaches. Int. J. Chem. Kinet., 2013, 45(9), 596-612.
[59]
Nasiri, F.; Bidar, M. A facile synthesis of stable 1, 4-diionic phosphorus compounds in aqueous media. Phosphorus Sulfur Silicon Relat. Elem., 2008, 183(6), 1344-1349.
[60]
Yavari, I.; Maghsoodlou, M.T. A facile synthesis of stable 1, 4-diionic phosphorus compounds. Tetrahedron Lett., 1998, 39(25), 4579-4580.
[61]
Yavari, I.; Islami, M.R.; Bijanzadeh, H.R. A facile synthesis of diastereoisomeric 1, 4-diionic organophosphorus compounds. Tetrahedron, 1999, 55(17), 5547-5554.
[62]
Yavari, I.; Anary-Abbasinejad, M.; Alizadeh, A. Synthesis and dynamic NMR study of atropisomerism in stable 1, 4-diionic phosphorus compounds. Phosphorus Sulfur Silicon Relat. Elem., 2002, 177(1), 93-103.
[63]
Shaabani, A.; Teimouri, M.B.; Yavari, I.; Arasi, H.N.; Bijanzadeh, H.R. 1, 4-Diionic organophosphorus compounds: Stereoselective synthesis of dialkyl 2-(1, 1, 1, 5, 5, 5-hexafluoro-2, 4-dioxo-pentane-3-yl-3-yide)-3-triphenylphosphoniobutane-1, 4-dioates. J. Fluor. Chem., 2000, 103(2), 155-157.
[64]
Yavari, I.; Hossaini, Z.; Alizadeh, A. Diastereoselective synthesis of meso-bisphosphonates from trialkyl (aryl) phosphites and activated acetylenes in the presence of 4-nitrophenol. Monatsh. Chem., 2006, 137(8), 1083-1088.
[65]
Maghsoodlou, M.T.; Hazeri, N.; Khorassani, S.M.H.; Nassiri, M.; Marandi, G.; Shahzadeh, A.G.; Bijanzadeh, H.R. Synthesis of hydroxybenzaldehyde stable phosphorus ylides from the reaction between acetylenic esters with triphenylphosphine in the presence of 2,3-dihydroxybenzaldehyde and 2-hydroxy-4-methoxybenz-aldehyde. Phosphorus Sulfur Silicon Relat. Elem., 2006, 181(5), 1117-1122.
[66]
Maghsoodlou, M.T.; Hazeri, N.; Habibi-Khorassani, S.M.; Moeeni, Z.; Marandi, G.; Lashkari, M.; Ghasemzadeh, M. Water-acetone media enforced chemoselective synthesis of 2-substituted pyrrole stable phosphorus ylides from reaction between pyrrole and acetylenic esters in the presence of triphenylphosphine. J. Chem. Res., 2007, 10, 566-568.
[67]
Burton, D.J.; Greenwald, J.R. The reaction of triphenylphosphine with trihalo-acid derivatives-a convenient preparation of α-halo vinyl esters and nitriles. Tetrahedron Lett., 1967, 8(16), 1535-1539.
[68]
Charati, F.R.; Maghsoodlou, M.T.; Khorassani, S.M.H.; Makha, M. Green diastereoselective synthesis of highly functionalised trifluoromethylated γ-lactone phosphonate esters bearing a thioester or ketothiophene. Tetrahedron Lett., 2008, 49(2), 343-347.
[69]
Maghsoodlou, M.T.; Hazeri, N.; Khorasani, S.M.H.; Moghaddam, H.M.; Nassiri, M.; Salehzadeh, J. A facile synthesis of stable phosphorus ylides containing chlorine and sulfur derived from 6-chloro-2-benzoxazolethiol and 2-chloro-phenothiazine. Phosphorus Sulfur Silicon Relat. Elem., 2009, 184(7), 1713-1721.
[70]
Heydari, R.; Maghsoodlou, M.T.; Yami, R.N. An efficient method for synthesis of organophosphorus compounds in aqueous media. Chin. Chem. Lett., 2009, 20(10), 1175-1178.
[71]
Neochoritis, C.G.; Zarganes-Tzitzikas, T.; Stephanidou-Stephanatou, J. Dimethyl acetylenedicarboxylate: A versatile tool in organic synthesis. Synthesis, 2014, 46(5), 537-585.
[72]
Khorassani, S.M.H.; Maghsoodlou, M.T.; Ebrahimi, A.; Roohi, H.; Zakarianezhad, M. UV spectrophotometric study of the kinetics and mechanism of the reactions between triphenylphosphine, dialkyl acetylenedicarboxylates and NH-acid. J. Iran. Chem. Soc., 2006, 3(3), 223-232.
[73]
Mostafa, S.; Khorassani, H.; Maghsoodlou, M.T.; Nassiri, M. HabibiKhorassani, S.M.; Maghsoodlou, M.T.; Nassiri, M.; Zakarianezhad, M.; Fattahi, M. Synthesis of stable phosphorus ylides from 3, 5-dimethylpyrazole and kinetic investigation of the reactions by UV spectrophotometry. ARKIVOC, 2006, 16(xvi), 168-184.
[74]
Yaghoubian, H.; Habibi-Khorassani, S.M.; Ebrahimi, A. Mechanistic and full kinetic study of the reaction between 4-chlorobenzaldehyde, malononitrile and dimedone using caffeine as a green catalyst. Orient. J. Chem., 2015, 31(4), 2107-2113.
[75]
Habibi, K.S.M.; Maghsoodlou, M.T.; Shahraki, M.; Poorshamsoddin, M.A.; Karima, M.; Abbasi, M. Sucrose catalyzes synthesis of 2-amino-4H-chromene: Insight to the kinetics. Iran. J. Catal., 2015, 5(1), 79-87.
[76]
Shahraki, M.; Habibi-khorassani, S.M. Kinetic aspects of tetrahydrobenzo [b] pyran formation in the presence of agar as a green catalyst : A mechanistic investigation. Biosci. Biotechnol. Res. Asia, 2016, 13(2), 715-723.
[77]
Pourpanah, S.S.; Habibi-Khorassani, S.M.; Shahraki, M. Fructose-catalyzed synthesis of tetrahydrobenzo [b] pyran derivatives: Investigation of kinetics and mechanism. Chin. J. Catal., 2015, 36(5), 757-763.
[78]
Ghodsi, F.; Habibi-Khorassani, S.M.; Shahraki, M. Kinetic spectrophotometric method for the 1, 4-diionic organophosphorus formation in the presence of Meldrum′ s Acid: Stopped-flow approach. Molecules, 2016, 21(11), pii 1514.
[79]
Ramazani, A.; Kazemizadeh, A.R.; Ahmadi, E.; Noshiranzadeh, N.; Souldozi, A. Synthesis and reactions of stabilized phosphorus ylides. Curr. Org. Chem., 2008, 12(1), 59-82.
[80]
Khorassani, S.M.H.; Ebrahimi, A.; Maghsoodlou, M.T.; Shahraki, M.; Price, D. Establishing a new conductance stopped-flow apparatus to investigate the initial fast step of reaction between 1, 1, 1-trichloro-3-methyl-3-phospholene and methanol under a dry inert atmosphere. Analyst, 2011, 136(8), 1713-1721.
[81]
Shahraki, M.; Habibi-Khorassani, S.M.; Dehdab, M. Effect of different substituents on the one-pot formation of 3, 4, 5-substituted furan-2 (5 H)-ones: A kinetics and mechanism study. RSC Adv, 2015, 5(65), 52508-52515.
[82]
Darijani, M.; Habibi-Khorassani, S.M.; Shahraki, M. A thermodynamic and kinetic insight into the pathways leading to a highly functionalized ketenimine: A computational study. Int. J. Chem. Kinet., 2015, 47(12), 751-763.
[83]
Habibi-khorassani, S.M.; Maghsoodluo, M.; Ebrahimi, A.; Ghalandarzehi, Y.; Ghodsi, F.; Asheri, O. A mechanistic investigation of stable phosphonate ester derived from 3, 4 dichloro aniline : A kinetics study. Orient. J. Chem., 2012, 28(3), 1153-1169.
[84]
Maghsoodlou, M.T.; Khorassani, S.M.H.; Hazeri, N.; Heydari, R.; Marandi, G.; Nassiri, M. The new γ-spiroiminolactone synthesis by reaction between alkyl or aryl isocyanides and 1, 10-phenanthroline-5, 6-dione in the presence of acetylenic esters. J. Chem. Res., 2006, 2006(4), 220-222.
[85]
Herbst, W.; Hunger, K. Industrial Organic Pigments: Production, Properties, Applications. John Wiley & Sons: New Jersy,, 2006.
[86]
Shahraki, M.; Khorassani, S.M.H.; Ebrahimi, A.; Maghsoodlou, M.T.; Paknahad, A. Theoretical, kinetic and mechanistic studies of the reaction between dialkyl acetylenedicarboxylates, triphenyl-phosphine and pyrrole in organic solvents. Prog. React. Kinet. Mech., 2012, 37(4), 321-343.
[87]
Shahraki, M.; Habibi-Khorassani, S.M. Kinetic spectrophotometric approach to the reaction mechanism of pyrrole phosphorus ylide formation based on monitoring the zwitterionic intermediate by using the stopped-flow technique. J. Phys. Org. Chem., 2015, 28(6), 396-402.
[88]
Maghsoodlou, M.T.; Hazeri, N.; Habibi-khorassani, S.M. Diastereoselective synthesis of phosphonato esters by reaction between triphenylphosphite and acetylenic esters in the presence of NH-acid compounds. ARKIVOC, 2006, 13(xiii), 117-123.
[89]
Ramazani, A.; Shajari, N.; Gouranlou, F. A facile synthetic approach to dimethyl 2-arylamino-3-(triphenylphosphor-anylidene) succinates from electron-poor primary arylamines. Phosphorus Sulfur Silicon Relat. Elem., 2001, 174(1), 223-227.
[90]
Hazeri, N.; Maghsoodlou, M.T.; Habibi-Khorassani, S.M.; Marandi, G.; Khandan-Barani, K.; Ziyaadini, M.; Aminkhani, A. Synthesis of novel 2-pyridyl-substituted 2, 5-dihydro-2-imino-and 2-amino-furan derivatives via a three component condensation of alkyl isocyanides and acetylenic esters with di-(2-pyridyl) ketone or 2-pyridinecarboxaldehyde. ARKIVOC, 2007, 1, 173-179.
[91]
Hazeri, N.; Maghsoodlou, M.T.; Habibi-Khorassani, S.M.; Ziyaadini, M.; Marandi, G.; Khandan-Barani, K.; Bijanzadeh, H.R. γ-Dispiro-iminolactone synthesis by three component reaction between alkyl isocyanides and acetylenic esters with α-dicarbonyl compounds. ARKIVOC, 2007, 13, 34-40.
[92]
Yavari, I.; Adib, M. Efficient synthesis of 5, 6, 7-trisubstituted 1H-pyrrolizines. Tetrahedron, 2001, 57(27), 5873-5878.
[93]
Esmaeili, A.A.; Islami, M.R.; Kardan-Moghaddam, G.R. One-pot synthesis of dialkyl succinates containing an α-amino group and a β-ylide moiety using electron-deficient acetylenic esters. Phosphorus Sulfur Silicon Relat. Elem., 2006, 181(3), 527-532.
[94]
Yavari, I.; Ahmadian-Razlighi, L. Triphenylphosphine-mediated reaction between dimethyl acetylenedicarboxylate and NH-acids derived from diaminobenzenes. Phosphorus Sulfur Silicon Relat. Elem., 2006, 181(4), 771-777.
[95]
Adib, M.; Sayahi, M.H. An efficient one-pot synthesis of 4H-pyrrolo [3, 2, 1-ij] quinolines. Monatshefte für . Chem., 2006, 137(2), 207-211.
[96]
Maghsoodlou, M.T.; Habibi, S.M.; Hazeri, N.; Nassiri, M. One-Pot synthesis of stable phosphorus ylides using CH- Acid compounds. Phosphorus Sulfur Silicon Relat. Elem., 2006, 181, 1363-1369.
[97]
Maghsoodlou, M.T.; Hazeri, N.; Khorasani, S.M.H.; Kakaei, R.; Nassiri, M. An efficient synthesis of stable phosphorus ylides derived from pyrazole and indazole. Phosphorus Sulfur Silicon Relat. Elem., 2006, 181(1), 25-30.
[98]
Maghsoodlou, M.T.; Khorasani, S.M.H.; Hazeri, N.; Nassiri, M. KaKaei, R.; Marandi, G. A simple synthesis of stable phosphoranes derived from imidazole derivatives. Phosphorus Sulfur Silicon Relat. Elem., 2006, 181(3), 553-560.
[99]
Maghsoodlou, M.T.; Hazeri, N.; Afshari, G.; Niroumand, U. A simple synthesis of stable phosphorus ylides derived from 2-benzoxazolinone and 2-mercaptobenzoxazole. Phosphorus Sulfur Silicon Relat. Elem., 2006, 181(12), 2681-2689.
[100]
Mostafa, S.; Khorassani, H.; Ebrahimi, A.; Maghsoodlou, M.T.; Karimi, P.; Kazemian, M.A. AIM analysis for the ylide rotamers from the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates in the presence of. Iran. J. Org. Chem., 2008, 1, 5-8.
[101]
Habibi-Khorassani, S.M.; Ebrahimi, A.; Maghsoodlou, M.T.; Ghahghayi, Z.; Ghasempour, H. NMR study and AIM analysis for assignment of the two Z-and E-isomers in phosphorane containing a 2-thiazoline-2-thiol. Arab. J. Chem., 2012, 5(1), 55-61.
[102]
Habibi-Khorassani, S.M.; Maghsoodlou, M.T.; Ebrahimi, A.; Heydari, R.; Hazeri, N.; Kazemian, M.A.; Nassiri, M.; Adrom, B.; Zakarianejad, M. Theoretical study and synthesis of the reaction between triphenylphosphine, dialkyl acetylenedicarb-oxylates and 2-aminobenzimidazole, 2-hydroxy-3-nitropyridine or 1, 2, 3, 4-tetrahydrocarbazole. Collect. Czechoslov. Chem. Commun., 2010, 75(8), 785-805.
[103]
Paknahad, A.; Khorassani, S.M.H.; Shahraki, M.; Rezvani, A.; Fard, M.A. Computational study for the ylide isomers from the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates in the presence of 6-chloro-2-benzoxazolethiol. Arab. J. Chem., 2015, 8(6), 885-891.
[104]
Khorassani, S.M.H.; Maghsoodlou, M.T.; Ghasempour, H.; Zakarianezhad, M.; Nassiri, M.; Ghahghaie, Z. AIM analysis, synthetic, kinetic and mechanistic investigations of the reaction between triphenylphosphine and dialkyl acetylenedicarboxylate in the presence of 3-methoxythiophenol. J. Chem. Sci., 2013, 125(2), 387-399.
[105]
Khorassani, S.M.H.; Ebrahimi, A.; Maghsoodlou, M.T.; Amin, M. Theoretical study, kinetics and mechanism investigation of the reactions between triphenylphosphine, dialkyl acetylene-dicarboxilates and NH-acid such as 2-ethylimidazole by UV. Mater. Sci. Res. India, 2008, 5(2), 235-250.
[106]
Shahraki, M.; Habibi-Khorassani, S.M.; Ebrahimi, A.; Maghsoodlou, M.; Ghalandarzehi, Y. Intramolecular hydrogen bonding in chemoselective synthesized 2-substituted pyrrole stable phosphorus ylide: GIAO, AIM, and NBO approaches. Struct. Chem., 2013, 24(2), 623-635.
[107]
Yavari, I.; Baharfar, R. New one-pot synthesis of tetra-alkoxycarbonylallylidenetriphenylphosphoranes. Tetrahedron Lett., 1998, 39(9), 1051-1054.
[108]
Habibi-Khorassani, S.M.; Maghsoodlou, M.T.; Ebrahimi, A.; Sameh-Salari, S.; Vasheghani-Farahani, F.; Kazemian, M.A. The variable temperature 1 H-NMR technique for kinetic investigation of equilibrium between the Z-and E-isomers in a especial ylide. Concepts Magn. Reson. Part A, 2013, 3(42A), 101-107.
[109]
Khorassani, S.M.H.; Maghsoodlou, M.T.; Ebrahimi, A.; Kazemian, M.A.; Salari, S.S.; Nasiri, S. 1H NMR kinetic investigation of the equilibrium between the Z-and E-isomers in a stable phosphorus ylide involving 2-mercaptobenzimidazole. Prog. React. Kinet. Mech., 2013, 38(3), 295-304.
[110]
Habibi-Khorassani, S.; Maghsoodlou, M.; Ebrahimi, A.; Aghdaei, E.; Kazemian, M. HNMR spectroscopic investigation of the kinetics of the equilibrium between Z and E isomers. Res. Chem. Intermed., 2014, 40(8), 2729-2736.
[111]
Aghdaei, E.; Habibi-Khorassani, S.M.; Shahraki, M. Variable temperatures 1HNMR technique on the kinetics and thermodynamic parameters of equilibrium between the Z and E isomers in a stable phosphorus ylide involving an imidazole. RSC Adv, 2016, 6(52), 46345-46349.
[112]
Asheri, O.; Habibi-Khorassani, S.M.; Shahraki, M. Synthesis and characterization of dimethyl 6-bromo-2 H-chromene-2, 3-dicarboxylate: Thermodynamic and kinetics investigations by computational and experimental studies. RSC Adv, 2016, 6(112), 111239-111249.


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VOLUME: 16
ISSUE: 1
Year: 2019
Page: [59 - 77]
Pages: 19
DOI: 10.2174/1570193X15666180612085855
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