How to cite this paper
Szczepanek, A., Jasińska, E., Kącka, A & Jasiński, R. (2015). An experimental and quantumchemical study of [2+3] cycloaddition between (Z)-C-(m,m,p-trimethoxyphenyl)-N-(p-methyphenyl)-nitrone and (E)-3,3,3-trichloro-1-nitroprop-1-ene: mechanistic aspects.Current Chemistry Letters, 4(1), 33-44.
Refrences
1. Huisgen R. (1984) in: 1,3-Dipolar Cycloaddition Chemistry, Padwa A. (Eds), Wiley Interscience, New York.
2. Huisgen R., Mloston G. (2004) in.: Modern Problem of Organic Chemistry: Potekhin A.A., Kostikov R.R., Baird M.S. (Eds) St. Petersburg University Press, St. Petersburg.
3. Jasiński R., Kwiatkowska M., Barański A. (2007) Mechanistyczne aspekty nieuzgodnionych (4+2)?-elektronowych cykloaddycji. Wiad. Chem., 61, 485-514.
4. Huisgen R., Pöchlauer P., Młostoń G., Polsborn K. (2007) Reactions of Di (tert?butyl) diazomethane with Acceptor?Substituted Ethylenes. Helv. Chim. Acta., 90, 983-998.
5. Quast H., Ach M., Ivanova S., Peters E-M., Peters K., von Schnering H.G. (1996) Ring Expansion of 2?Alkylidenedihydroquinolines to 2?Iminodihydro?1?benzazepines by Phenyl, Methanesulphonyl, and Trifluoromethanesulphonyl Azide. Liebigs Ann. Chem., 1551-1558.
6. Krompiec S, Bujak P., Malarz J., Krompiec M., Skórka Ł., Pluta T., Danikiewicz W., Kania M., Kusz J. (2012) An isomerization – 1,3-dipolar cycloaddition tandem reaction towards the synthesis of 3-aryl-4-methyl-5-O-substituted isoxazolines from O-allyl compounds. Tetrahedron, 68, 6018-6031.
7. Bujak P., Krompiec S., Malarz J., Krompiec M., Filapek M., Danikiewicz W., Kania M., G?barowska K., Grudzka I. (2010) Synthesis of 5-aminoisoxazolines from N-allyl compounds and nitryle oxides via tandemisomerization - 1,3-dipolar cycloaddition. Tetrahedron, 66, 5972-5981.
8. Huisgen R., Giera H., Mloston G. (2005) 2,2,6,6-Tetramethylcyclohexanethione
S-methylide, a highly hindered thiocarbonyl ylide: two-step cycloadditions. Tetrahedron, 61, 6143-6153.
9. Mloston G., Huisgen R., Giera H. (2002) Reactions of a sterically hindered tetrasubstituted thiocarbonyl ylide with acceptor-substituted ethylenes; regioselectivity and stereochemistry. Tetrahedron, 58, 4185-4193.
10. Huisgen R., Mloston G., Langhals E. (2001) Cycloadditions of & apos; thiocarbonyl ylides & apos; with tetracyanoethylene (=ethenetetracarbonitrile): Interception of intermediates. Helv. Chim. Acta., 84, 1805-1820.
11. Elender K., Riebel P., Weber A., Sauer J. (2000) 1,3-Dipolar Cycloaddition Reactions of Stable Bicyclic and Monocyclic Azomethine Ylides: Kinetic Aspects. Tetrahedron, 56, 4261-4265.
12. Jasi?ski R., (2004) in: PhD Thesis, Cracow University of Technology.
13. Jasi?ski R., Bara?ski A. (2006) Mechanistic study on the [2+3] Cycloaddition of Z-C,N-diphenylnitrone with trans-1-nitropropene-1 and trans-3,3,3-trichloro-1-nitroproene-1. Polish J. Chem., 80, 1493-1502.
14. Chattaraj P.K., Giri G., Duley S. (2011) Update 2 of: Electrophilicity index, Chem. Rev., 111, PR43-PR75.
15. Jasi?ski R. (2012) Exploration of regiospecificity phenomenon in [2+3] cycloaddition reactions between arylnitrones and trans-substituted nitroethenes on the basis of the reactivity indices theory. Current Chem. Lett., 1, 157.
16. Perez P., Domingo L.R., Aizman A., Contreras R. (2007) in: Theoretical and Computational Chemistry, Toro-Labbé A. (Eds), vol. 19, Elsevier.
17. Kapłon K., Demchuk O.M., Wieczorek M., Pietrusiewicz K.M. (2014) Brönsted acid catalyzed direct oxidative arylation of 1,4-naphthoquinone. Current Chem. Lett., 3, 23.
18. Domingo L.R., Perez P., Saez J.A. (2014) Understanding the local reactivity in polar organic reactions through electrophilic and nucleophilic Parr functions, RSC Adv., 3, 1486-1494.
19. Perez P., Domingo L.R., Duque-Norena M., Chamorro E. (2009) A condensed-to-atom nucleophilicity index. An application to the director effects on the electrophilic aromatic substitutions. J. Mol. Struct. (TheoChem), 895, 86-91.
20. Reichardt Ch. (1990) Solvents and Solvent Effects in Organic Chemistry, VCH, Weinheim.
21. Schwetlick K. (1971) Kinetische Metoden zur Untersuchung von Reaktionsmechanismen, VEB, Berlin.
22. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman R.J., Montgomery J.A., Vreven T.Jr., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima Y., Honda O., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas M.C., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin L.R., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C.,. Pople J.A. (2003) Gaussian 03, Revision B.04, Gaussian, Inc., Pittsburgh PA.
23. Domingo L.R., Benchouk W., Mekelleche S.M. (2007) Understanding the role of the Lewis acid catalyst on the 1,3-dipolar cycloaddition of N-benzylideneaniline N-oxide with acrolein: a DFT study. Tetrahedron, 63, 4464-4471.
24. Jasiński R. (2013) Competition between the one-step and two-step, zwitterionic mechanisms in the [2+3] cycloaddition of gem-dinitroethene with (Z)-C,N-diphenylnitrone: a DFT computational study. Tetrahedron, 69, 927-932.
25. Acharjee N., Banerji A. (2011) DFT interpretation of 1,3-dipolar cycloaddition reaction of C,N-diphenyl nitrone to methyl crotonate in terms of reactivity indices, interaction energy and activation parameters. Comput. Theor. Chem., 967, 50-58.
26. Jasi?ski R. (2009) Regio- and stereoselectivity of [2+3]cycloaddition of nitroethene to (Z)-N-aryl-C-phenylnitrones. Collect. Czech. Chem. Commun., 74, 1341-1349.
27. Leroy G., Sana M., Burke L.A., Nguyen M.T. (1980) Contribution to the Theoretical Study of Reaction Mechanisms. Quantum Theory Chem. React., 1, 91-144.
28. Kiselev V.D., Konovalov A.I. (2009) Internal and external factors influencing the Diels–Alder reaction. J. Phys. Org. Chem., 22, 466-483.
29. Rundel W. (1968) in: Houben-Weyl. Methoden der Organischen Chemie, Vol. 10/4, Thieme Verlag, Stuttgart.
30. Brower F., Burkett H. (1953) 1,1,1-Trichloro-2-arylamino-3-nitropropanes, J. Am. Chem. Soc., 75, 1082-1084.
31. Jasi?ski R. (2013) in: Preparatyka alifatycznych nitrozwizk?w, RTN, Radom.
32. Parr R.G., Yang W. (1989) in: Density Functional Theory of Atoms and Molecules, Oxford University, New York.
33. Cossi M., Rega N., Scalmani G., Barone V. (2003) Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. J. Comp. Chem., 24, 669-681.
2. Huisgen R., Mloston G. (2004) in.: Modern Problem of Organic Chemistry: Potekhin A.A., Kostikov R.R., Baird M.S. (Eds) St. Petersburg University Press, St. Petersburg.
3. Jasiński R., Kwiatkowska M., Barański A. (2007) Mechanistyczne aspekty nieuzgodnionych (4+2)?-elektronowych cykloaddycji. Wiad. Chem., 61, 485-514.
4. Huisgen R., Pöchlauer P., Młostoń G., Polsborn K. (2007) Reactions of Di (tert?butyl) diazomethane with Acceptor?Substituted Ethylenes. Helv. Chim. Acta., 90, 983-998.
5. Quast H., Ach M., Ivanova S., Peters E-M., Peters K., von Schnering H.G. (1996) Ring Expansion of 2?Alkylidenedihydroquinolines to 2?Iminodihydro?1?benzazepines by Phenyl, Methanesulphonyl, and Trifluoromethanesulphonyl Azide. Liebigs Ann. Chem., 1551-1558.
6. Krompiec S, Bujak P., Malarz J., Krompiec M., Skórka Ł., Pluta T., Danikiewicz W., Kania M., Kusz J. (2012) An isomerization – 1,3-dipolar cycloaddition tandem reaction towards the synthesis of 3-aryl-4-methyl-5-O-substituted isoxazolines from O-allyl compounds. Tetrahedron, 68, 6018-6031.
7. Bujak P., Krompiec S., Malarz J., Krompiec M., Filapek M., Danikiewicz W., Kania M., G?barowska K., Grudzka I. (2010) Synthesis of 5-aminoisoxazolines from N-allyl compounds and nitryle oxides via tandemisomerization - 1,3-dipolar cycloaddition. Tetrahedron, 66, 5972-5981.
8. Huisgen R., Giera H., Mloston G. (2005) 2,2,6,6-Tetramethylcyclohexanethione
S-methylide, a highly hindered thiocarbonyl ylide: two-step cycloadditions. Tetrahedron, 61, 6143-6153.
9. Mloston G., Huisgen R., Giera H. (2002) Reactions of a sterically hindered tetrasubstituted thiocarbonyl ylide with acceptor-substituted ethylenes; regioselectivity and stereochemistry. Tetrahedron, 58, 4185-4193.
10. Huisgen R., Mloston G., Langhals E. (2001) Cycloadditions of & apos; thiocarbonyl ylides & apos; with tetracyanoethylene (=ethenetetracarbonitrile): Interception of intermediates. Helv. Chim. Acta., 84, 1805-1820.
11. Elender K., Riebel P., Weber A., Sauer J. (2000) 1,3-Dipolar Cycloaddition Reactions of Stable Bicyclic and Monocyclic Azomethine Ylides: Kinetic Aspects. Tetrahedron, 56, 4261-4265.
12. Jasi?ski R., (2004) in: PhD Thesis, Cracow University of Technology.
13. Jasi?ski R., Bara?ski A. (2006) Mechanistic study on the [2+3] Cycloaddition of Z-C,N-diphenylnitrone with trans-1-nitropropene-1 and trans-3,3,3-trichloro-1-nitroproene-1. Polish J. Chem., 80, 1493-1502.
14. Chattaraj P.K., Giri G., Duley S. (2011) Update 2 of: Electrophilicity index, Chem. Rev., 111, PR43-PR75.
15. Jasi?ski R. (2012) Exploration of regiospecificity phenomenon in [2+3] cycloaddition reactions between arylnitrones and trans-substituted nitroethenes on the basis of the reactivity indices theory. Current Chem. Lett., 1, 157.
16. Perez P., Domingo L.R., Aizman A., Contreras R. (2007) in: Theoretical and Computational Chemistry, Toro-Labbé A. (Eds), vol. 19, Elsevier.
17. Kapłon K., Demchuk O.M., Wieczorek M., Pietrusiewicz K.M. (2014) Brönsted acid catalyzed direct oxidative arylation of 1,4-naphthoquinone. Current Chem. Lett., 3, 23.
18. Domingo L.R., Perez P., Saez J.A. (2014) Understanding the local reactivity in polar organic reactions through electrophilic and nucleophilic Parr functions, RSC Adv., 3, 1486-1494.
19. Perez P., Domingo L.R., Duque-Norena M., Chamorro E. (2009) A condensed-to-atom nucleophilicity index. An application to the director effects on the electrophilic aromatic substitutions. J. Mol. Struct. (TheoChem), 895, 86-91.
20. Reichardt Ch. (1990) Solvents and Solvent Effects in Organic Chemistry, VCH, Weinheim.
21. Schwetlick K. (1971) Kinetische Metoden zur Untersuchung von Reaktionsmechanismen, VEB, Berlin.
22. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman R.J., Montgomery J.A., Vreven T.Jr., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima Y., Honda O., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas M.C., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin L.R., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C.,. Pople J.A. (2003) Gaussian 03, Revision B.04, Gaussian, Inc., Pittsburgh PA.
23. Domingo L.R., Benchouk W., Mekelleche S.M. (2007) Understanding the role of the Lewis acid catalyst on the 1,3-dipolar cycloaddition of N-benzylideneaniline N-oxide with acrolein: a DFT study. Tetrahedron, 63, 4464-4471.
24. Jasiński R. (2013) Competition between the one-step and two-step, zwitterionic mechanisms in the [2+3] cycloaddition of gem-dinitroethene with (Z)-C,N-diphenylnitrone: a DFT computational study. Tetrahedron, 69, 927-932.
25. Acharjee N., Banerji A. (2011) DFT interpretation of 1,3-dipolar cycloaddition reaction of C,N-diphenyl nitrone to methyl crotonate in terms of reactivity indices, interaction energy and activation parameters. Comput. Theor. Chem., 967, 50-58.
26. Jasi?ski R. (2009) Regio- and stereoselectivity of [2+3]cycloaddition of nitroethene to (Z)-N-aryl-C-phenylnitrones. Collect. Czech. Chem. Commun., 74, 1341-1349.
27. Leroy G., Sana M., Burke L.A., Nguyen M.T. (1980) Contribution to the Theoretical Study of Reaction Mechanisms. Quantum Theory Chem. React., 1, 91-144.
28. Kiselev V.D., Konovalov A.I. (2009) Internal and external factors influencing the Diels–Alder reaction. J. Phys. Org. Chem., 22, 466-483.
29. Rundel W. (1968) in: Houben-Weyl. Methoden der Organischen Chemie, Vol. 10/4, Thieme Verlag, Stuttgart.
30. Brower F., Burkett H. (1953) 1,1,1-Trichloro-2-arylamino-3-nitropropanes, J. Am. Chem. Soc., 75, 1082-1084.
31. Jasi?ski R. (2013) in: Preparatyka alifatycznych nitrozwizk?w, RTN, Radom.
32. Parr R.G., Yang W. (1989) in: Density Functional Theory of Atoms and Molecules, Oxford University, New York.
33. Cossi M., Rega N., Scalmani G., Barone V. (2003) Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. J. Comp. Chem., 24, 669-681.