How to cite this paper
APA: Zakarianejad, M., Habibi-Khorassani, S., Makiabadi, B & Taheri, A. (2013). Structural effects of different NH-acids and dialkyl acetylenedicarboxylates on the kinetic parameters of stable phosphorus ylids: a mechanistic investigation. Current Chemistry Letters, 2(2), 93-104.
Chicago/Turabian: Zakarianejad, M., Habibi-Khorassani, S., Makiabadi, B & Taheri, A. 2013. "Structural effects of different NH-acids and dialkyl acetylenedicarboxylates on the kinetic parameters of stable phosphorus ylids: a mechanistic investigation." Current Chemistry Letters 2, no. 2 (2013): 93-104.
AMA: 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. Current Chemistry Letters. 2013;2(2):93-104.
References
1. Crayson M., and Griffith E. J. (1972) Topics in Phosphorus Chemistry, vol. 7. Insterscience, New York.
2. Hudson H. R. (1990) Primary, Secondary and Tertiary Phosphines, Plyphosphines and Heterocyclic Organophosphorus Compounds, in the Chemistry of Organophosphorus Compounds. Wiley: New York, 1, 386-472.
3. Engel R. (1988) Synthesis of Carbon-phosphorus Bonds. CRC Press: Boca Rotan, FL, 1988.
4. Cadogan J. I. G. (1979) Organophosphorus Reagent in Organic Synthesis, Academic press: New York.
5. Ramazani A., Noshiranzadeh N., and Ghamkhari A., (2008) One-pot diastereoselective synthesis of densely functionalized 2-H indeno [2,1-b] furans. Single-crystal X-ray structure of dimethyl 8,8a-dihydro-8-oxo-8a-(2,2,2-trichloroethoxy)-2H-indeno [2,1-b] furan- 2,3-dicarboxylate. Helv. Chim. Acta., 91, 2252-2261.
6. Ramazani A., Kazemizadeh A. R., Ahmadi E., Noshiranzadeh N., and Souldozi A. (2001) Synthesis and reactions of stabilized phosphorus ylides. Curr. Org. Chem., 2, 59-82.
7. Maryanoff B. E., and Reitz A. B. (1989) The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects. Chem. Rev., 89, 863-927.
8. Maghsoodlou M. T., Hazeri N., Habibi-Khorassani S. M., Moeeni Z., Marandi Gh., Lashkari M., Ghasemzadeh M., and Bijanzadeh H. R. (2007) 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., 566-568.
9. Anary-Abbasinejad M., Anaraki-Ardakani H., and Hosseini-Mehdiabad H. (2008) One-pot synthesis of stable phosphorus ylides by three-component reaction between dimethyl acetylenedicarboxylate, semicarbazones, and triphenylphosphine. Phosphorus Sulfur and Silicon, 183, 1440-1446.
10. Hassanabadi A., Anary-Abbasinejad M., and Dehghan A. (2009) Three-component reaction of triphenylphosphine, dimethyl acetylenedicarboxylate, and aldehyde benzoylhydrazones: an efficient one-pot synthesis of stable phosphorus ylides. Synth. Commun., 39, 132-138.
11. Anaraki-Ardakani H., Sadeghian Sh., Rastegari F., Hassanabadi A., and Anary-Abbasinejad M. (2008) Three-component reaction of triphenylphosphine, acetylenic esters, and arylsulfonyl hydrazines: an efficient one-pot synthesis of stable ?- nitrogen-substituted phosphourus ylides. Synth. Commun., 38, 1990-1999.
12. Yavari I., Adib M., Jahani-Mogaddam F., and Sayahi M. H. (2002) A simple synthesis of stable heterocyclic phosphorus ylides derived from NH-acids. Phosphorus Sulfur and Silicon, 177, 545-553.
13. Kazemian M. A., Nassiri M., Ebrahimi A., Maghsoodlou M. T., and Habibi-Khorassani S. M. (2008) A facile synthesis, dynamic 1H NMR, and theoretical study of novel stable heterocyclic phosphorus ylides containing a tetrazole ring. Arkivoc, (xvii), 173-183.
14. Fitjer L., and Quabeck U. (1985) The Wittig reaction using potassium-tert-butoxide high yield methylenations of sterically hindered ketones. Synth. Commun., 15, 855-864.
15. Ramazani A., and Souldozi A. (2005) Dipotassium-hydrogen-phosphate-powder-catalyzed stereoselective C-vinylation of diphenylacetonitril. Phosphorus Sulfur Silicon, 180, 2801-2804.
16. Yavari I., and Alizadeh A. A. (2003) A simple approach to the synthesis of 1, 4-bis (arylsulfonyl) tetrahydropyrazine-2, 5-diones. Monatsh. Chem., 134, 435-438.
17. Ramazani A., and Bodaghi A. (2000) One-pot, four-component synthesis of dialkyl [indane-1, 3-dione-2-ylidene] alkoxysuccinates. Tetrahedron Lett., 41, 567-568.
18. Wang Z. G., Zhang G. T., Guzei I., and Verkade J. G. (2001) PhCH=P (MeNCH2CH2)3N: A novel ylide for quantitative E selectivity in the wittig reaction. J. Org. Chem., 66, 3521-3524.
19. Islami M. R., Hassani Z., and Saidi K. (2003) An efficient and rapid one-pot synthesis of highly functionalized stable phosphorus ylides containing the sulfur atom. Synth. Commun., 33, 65-72.
20. Keglevich G., Baan Z.,and Hermecz I. (2007) The phosphorus aspects of green chemistry: the use of quaternary phosphonium salts and 1,3-dialkylimidazolium hexafluorophosphates in organic synthesis. Curr. Org. Chem., 11, 107-126.
21. Yavari, I., and Ahmadian-Rezlighi L. (2006) Triphenylphosphine-mediated reaction between dimethyl acetylenedicarboxylate and NH-acids derived from diaminobenzenes. Phosphorus Sulfur and Silicon, 181, 771-777.
22. Adib M., Mostofi M., Ghanbary K., and Bijanzadeh H. R. (2005) Vinyltriphenylphosphonium salt-mediated efficient synthesis of iminophosphoranes derived from 2-aminothiazoles. Synthesis, 10, 1663-1668.
23. Kalantari M., Islami M. R., Hassani Z., and Saidi K. (2006) Synthesis of dimethyl-1-(trifluoromethyl)-3H-pyrrolizine-2, 3-dicarboxylate using phosphorus compounds. Arkivoc, (x), 55-62.
24. Islami M. R., Mollazehi F., Badiei A., and Sheibani H. (2005) Serendipitous synthesis of 1, 4-benzothiazin derivatives using 2-[(2-aminophenyl)disulfanyl aniline, Arkivoc, (xv), 25-29.
25. Maghsoodlou M. T., Habibi-Khorassani S. M., Rofouei M. K., Adhamdoust S. R., and Nassiri M. (2006) Triphenylphosphite as a good reagent for the diasteroselective synthesis of phosphonate esters. Arkivoc, (xii), 145-151.
26. Maghsoodlou M. T., Hazeri N., Habibi-Khorassani S. M., Ghulame-Shahzadeh A., and Nassiri M. (2006) A simple synthesis of stable phosphorus ylides from indole and some of its derivatives. Phosphorus Sulfur and Silicon, 181, 913-919.
27. Habibi-Khorassani S. M., Maghsoodlou M. T., Ebrahimi A., Zakarianejad M., and Fattahi M. (2007) Kinetics and mechanism of the reactions between triphenylphosphine, dialkyl acetylenedicarboxilates and a NH-acid, pyrazole, by UV spectrophotometry. J. Soln. Chem., 36, 1117-1127.
28. Sasaki S., and Yoshifuji M. (2001) Synthesis, structure and properties of crowded triarylphosphines. Curr. Org. Chem., 11, 17-31.
29. Habibi-Khorassani S. M., Maghsoodlou M. T., Nassiri M., Zakarianejad M., and Fattahi M. (2006) Synthesis of stable phosphorus ylides from 3, 5-dimethylpyrazoleand kinetic investigation of the reactions by UV spectrophotometry. Arkivoc, (xvi), 168-184.
30. Maghsoodlou M. T., Habibi Khorassani S. M., Hazeri, N., Kakaei, R., Nassiri, M., and Marandi G. (2006). An efficient synthesis of stable phosphorus ylides derived from triphenylphosphine, dialkyl acetylenedicarboxylates, and an NH-Acid. Phosphorus, Sulfur and Silicon, 181, 4, 865-877.
31. Schwartz L. M., and Gelb R. I. (1978) Alternative method of analyzing first-order kinetic data. Anal. Chem. 50, 11, 1592-1594.
2. Hudson H. R. (1990) Primary, Secondary and Tertiary Phosphines, Plyphosphines and Heterocyclic Organophosphorus Compounds, in the Chemistry of Organophosphorus Compounds. Wiley: New York, 1, 386-472.
3. Engel R. (1988) Synthesis of Carbon-phosphorus Bonds. CRC Press: Boca Rotan, FL, 1988.
4. Cadogan J. I. G. (1979) Organophosphorus Reagent in Organic Synthesis, Academic press: New York.
5. Ramazani A., Noshiranzadeh N., and Ghamkhari A., (2008) One-pot diastereoselective synthesis of densely functionalized 2-H indeno [2,1-b] furans. Single-crystal X-ray structure of dimethyl 8,8a-dihydro-8-oxo-8a-(2,2,2-trichloroethoxy)-2H-indeno [2,1-b] furan- 2,3-dicarboxylate. Helv. Chim. Acta., 91, 2252-2261.
6. Ramazani A., Kazemizadeh A. R., Ahmadi E., Noshiranzadeh N., and Souldozi A. (2001) Synthesis and reactions of stabilized phosphorus ylides. Curr. Org. Chem., 2, 59-82.
7. Maryanoff B. E., and Reitz A. B. (1989) The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects. Chem. Rev., 89, 863-927.
8. Maghsoodlou M. T., Hazeri N., Habibi-Khorassani S. M., Moeeni Z., Marandi Gh., Lashkari M., Ghasemzadeh M., and Bijanzadeh H. R. (2007) 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., 566-568.
9. Anary-Abbasinejad M., Anaraki-Ardakani H., and Hosseini-Mehdiabad H. (2008) One-pot synthesis of stable phosphorus ylides by three-component reaction between dimethyl acetylenedicarboxylate, semicarbazones, and triphenylphosphine. Phosphorus Sulfur and Silicon, 183, 1440-1446.
10. Hassanabadi A., Anary-Abbasinejad M., and Dehghan A. (2009) Three-component reaction of triphenylphosphine, dimethyl acetylenedicarboxylate, and aldehyde benzoylhydrazones: an efficient one-pot synthesis of stable phosphorus ylides. Synth. Commun., 39, 132-138.
11. Anaraki-Ardakani H., Sadeghian Sh., Rastegari F., Hassanabadi A., and Anary-Abbasinejad M. (2008) Three-component reaction of triphenylphosphine, acetylenic esters, and arylsulfonyl hydrazines: an efficient one-pot synthesis of stable ?- nitrogen-substituted phosphourus ylides. Synth. Commun., 38, 1990-1999.
12. Yavari I., Adib M., Jahani-Mogaddam F., and Sayahi M. H. (2002) A simple synthesis of stable heterocyclic phosphorus ylides derived from NH-acids. Phosphorus Sulfur and Silicon, 177, 545-553.
13. Kazemian M. A., Nassiri M., Ebrahimi A., Maghsoodlou M. T., and Habibi-Khorassani S. M. (2008) A facile synthesis, dynamic 1H NMR, and theoretical study of novel stable heterocyclic phosphorus ylides containing a tetrazole ring. Arkivoc, (xvii), 173-183.
14. Fitjer L., and Quabeck U. (1985) The Wittig reaction using potassium-tert-butoxide high yield methylenations of sterically hindered ketones. Synth. Commun., 15, 855-864.
15. Ramazani A., and Souldozi A. (2005) Dipotassium-hydrogen-phosphate-powder-catalyzed stereoselective C-vinylation of diphenylacetonitril. Phosphorus Sulfur Silicon, 180, 2801-2804.
16. Yavari I., and Alizadeh A. A. (2003) A simple approach to the synthesis of 1, 4-bis (arylsulfonyl) tetrahydropyrazine-2, 5-diones. Monatsh. Chem., 134, 435-438.
17. Ramazani A., and Bodaghi A. (2000) One-pot, four-component synthesis of dialkyl [indane-1, 3-dione-2-ylidene] alkoxysuccinates. Tetrahedron Lett., 41, 567-568.
18. Wang Z. G., Zhang G. T., Guzei I., and Verkade J. G. (2001) PhCH=P (MeNCH2CH2)3N: A novel ylide for quantitative E selectivity in the wittig reaction. J. Org. Chem., 66, 3521-3524.
19. Islami M. R., Hassani Z., and Saidi K. (2003) An efficient and rapid one-pot synthesis of highly functionalized stable phosphorus ylides containing the sulfur atom. Synth. Commun., 33, 65-72.
20. Keglevich G., Baan Z.,and Hermecz I. (2007) The phosphorus aspects of green chemistry: the use of quaternary phosphonium salts and 1,3-dialkylimidazolium hexafluorophosphates in organic synthesis. Curr. Org. Chem., 11, 107-126.
21. Yavari, I., and Ahmadian-Rezlighi L. (2006) Triphenylphosphine-mediated reaction between dimethyl acetylenedicarboxylate and NH-acids derived from diaminobenzenes. Phosphorus Sulfur and Silicon, 181, 771-777.
22. Adib M., Mostofi M., Ghanbary K., and Bijanzadeh H. R. (2005) Vinyltriphenylphosphonium salt-mediated efficient synthesis of iminophosphoranes derived from 2-aminothiazoles. Synthesis, 10, 1663-1668.
23. Kalantari M., Islami M. R., Hassani Z., and Saidi K. (2006) Synthesis of dimethyl-1-(trifluoromethyl)-3H-pyrrolizine-2, 3-dicarboxylate using phosphorus compounds. Arkivoc, (x), 55-62.
24. Islami M. R., Mollazehi F., Badiei A., and Sheibani H. (2005) Serendipitous synthesis of 1, 4-benzothiazin derivatives using 2-[(2-aminophenyl)disulfanyl aniline, Arkivoc, (xv), 25-29.
25. Maghsoodlou M. T., Habibi-Khorassani S. M., Rofouei M. K., Adhamdoust S. R., and Nassiri M. (2006) Triphenylphosphite as a good reagent for the diasteroselective synthesis of phosphonate esters. Arkivoc, (xii), 145-151.
26. Maghsoodlou M. T., Hazeri N., Habibi-Khorassani S. M., Ghulame-Shahzadeh A., and Nassiri M. (2006) A simple synthesis of stable phosphorus ylides from indole and some of its derivatives. Phosphorus Sulfur and Silicon, 181, 913-919.
27. Habibi-Khorassani S. M., Maghsoodlou M. T., Ebrahimi A., Zakarianejad M., and Fattahi M. (2007) Kinetics and mechanism of the reactions between triphenylphosphine, dialkyl acetylenedicarboxilates and a NH-acid, pyrazole, by UV spectrophotometry. J. Soln. Chem., 36, 1117-1127.
28. Sasaki S., and Yoshifuji M. (2001) Synthesis, structure and properties of crowded triarylphosphines. Curr. Org. Chem., 11, 17-31.
29. Habibi-Khorassani S. M., Maghsoodlou M. T., Nassiri M., Zakarianejad M., and Fattahi M. (2006) Synthesis of stable phosphorus ylides from 3, 5-dimethylpyrazoleand kinetic investigation of the reactions by UV spectrophotometry. Arkivoc, (xvi), 168-184.
30. Maghsoodlou M. T., Habibi Khorassani S. M., Hazeri, N., Kakaei, R., Nassiri, M., and Marandi G. (2006). An efficient synthesis of stable phosphorus ylides derived from triphenylphosphine, dialkyl acetylenedicarboxylates, and an NH-Acid. Phosphorus, Sulfur and Silicon, 181, 4, 865-877.
31. Schwartz L. M., and Gelb R. I. (1978) Alternative method of analyzing first-order kinetic data. Anal. Chem. 50, 11, 1592-1594.