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Number of results

Journal

2011 | 9 | 6 | 1008-1018

Article title

A B3LYP/6-31G(d) study of Diels-Alder reactions between cyclopentadiene and (E)-2-arylnitroethenes

Content

Title variants

Languages of publication

EN

Abstracts

EN
The B3LYP/6-31G(d) simulations of competing CDA and HDA reactions between cyclopentadiene and (E)-2-arylnitroethenes prove that regardless of the medium polarity, the processes leading to respective 5-nitro-6-aryl-bicyclo-[2,2,0]-hept-2-enes 3,4 (paths A and B) should be most favoured, and the more electrophilic (E)-2-(p-nitrophenyl)-nitroethene should be more reactive than the less electrophilic (E)-2-(p-methoxyphenyl)-nitroethene. Asymmetry of the transition complexes on the favoured pathways increases with increase of medium polarity, but not sufficiently to enforce the zwitterionic mechanism. Analysis of competing pathways leading to HDA adducts proves that not all these compounds can be formed directly from the adducts. In particular, on the path C, the initially formed 5-nitro-6-aryl-bicyclo-[2,2,0]-hept-2-enes 3 is converted to 2-phenyl-4-aza-5-oxy-bicyclo-[3,4,0]-nona-3,7-diene N-oxides 5 as a result of a [3.3]-sigmatropic shift. On the paths D–F leading to 2-phenyl-4-aza-5-oxy-bicyclo-[3,4,0]-nonadienes N-oxides 6–8, the reaction proceeds according to a one-step mechanism. [...]

Publisher

Journal

Year

Volume

9

Issue

6

Pages

1008-1018

Physical description

Dates

published
1 - 12 - 2011
online
27 - 9 - 2011

Contributors

  • Institute of Organic Chemistry and Technology, Cracow University of Technology, 31155, Cracow, Poland
author
  • Faculty of Organic Chemistry and Technology, Ivanovo State University of Chemistry and Technology, 153000, Ivanovo, Russian Federation
  • Institute of Organic Chemistry and Technology, Cracow University of Technology, 31155, Cracow, Poland

References

  • [1] R. Jasiński, O.I. Koifman, A. Barański, Mendeleev Commun. (2011) (In press)
  • [2] R. Jasiński, M. Kwiatkowska, A. Barański, J. Phys. Org. Chem. (2011) (In press) DOI: 10.1002/poc.1853 [Crossref]
  • [3] R. Jasiński, P. Michorczyk, E. Jasińska, O. Koifman, A. Barański, Izv. Vuzov. Khimya i Khim. Tekhnol. 54, 89 (2011) (In Russian)
  • [4] R. Jasiński, A. Barański, J. Mol. Struct. (TheoChem) 949, 8 (2010) http://dx.doi.org/10.1016/j.theochem.2010.02.023[Crossref]
  • [5] R. Jasiński, M. Rzyman, A. Barański., Coll. Czech. Chem. Commun. 75, 919 (2010) http://dx.doi.org/10.1135/cccc2009562[Crossref]
  • [6] M. Kwiatkowska, R. Jasiński, M. Mikulska, A. Barański, Monatsh. Chem. 141, 545 (2010) http://dx.doi.org/10.1007/s00706-010-0292-6[Crossref]
  • [7] R. Jasiński, M. Kwiatkowska, A. Barański, J. Mol. Struct. (TheoChem) 910, 80 (2009). http://dx.doi.org/10.1016/j.theochem.2009.06.018[Crossref]
  • [8] M.I. Mangione, A.M. Sarotti, A.G. Suárez, R.A. Spanevello, Carbohydrate Research 346, 460 (2011) http://dx.doi.org/10.1016/j.carres.2010.12.006[Crossref]
  • [9] R.S. Paton, J.L. Mackey, W.H. Kim, J.H. Lee, S.J. Danishefsky, K.N. Houk, J. Am. Chem. Soc. 132, 9335 (2010) http://dx.doi.org/10.1021/ja1009162[Crossref]
  • [10] M.V. Gomez, A.I. Aranda, A. Moreno, F.P. Cossıo, A. Cozar, A. Dıaz-Ortiz, A. Hoz, P. Prieto, Tetrahedron 65, 5328 (2009) http://dx.doi.org/10.1016/j.tet.2009.04.065[Crossref]
  • [11] N. Çelebi-Ölçüm, D.H. Ess, V. Aviyente, K.N. Houk, J. Org. Chem. 73, 7472 (2008). http://dx.doi.org/10.1021/jo801076t[Crossref]
  • [12] N. Ono, The nitro group in organic synthesis (Wiley-VCH, Weinheim, 2001) http://dx.doi.org/10.1002/0471224480[Crossref]
  • [13] S.E. Denmark, A. Thorarensen, Chem. Rev. 96, 137 (1996) http://dx.doi.org/10.1021/cr940277f[Crossref]
  • [14] P. Perez, L.R. Domingo, A. Aizman, R. Contreras, In: A. Toro-Labbé (Ed.), Theoretical and Computational Chemistry (Elsevier, Amsterdam, 2007) vol. 19
  • [15] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Jr. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, Y. Nakajima, O. Honda, O. Kitao, H. Nakai, M. Klene, X Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, M.C., Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D. J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez,. J.A. Pople, Gaussian 03, Revision B.04 (Gaussian, Inc., Pittsburgh PA, 2003)
  • [16] M. Barone, M. Cossi, J. Tomasi, J. Comp. Chem. 19, 404 (1998) http://dx.doi.org/10.1002/(SICI)1096-987X(199803)19:4<404::AID-JCC3>3.0.CO;2-W[Crossref]
  • [17] R.K. Nesbet, Variational principles and methods in theoretical physics and chemistry (Cambridge University Press, Cambridge, 2003)
  • [18] M. Bujak, A. Barański, Czasopismo Tech. PK. (Chemia), 1 (2002) (In Polish); Chem. Abstr. 140, 270441
  • [19] V.D. Kiselev, A.I. Konovalov, Russ. Chem. Bull., Int. Ed. 52, 293 (2003) http://dx.doi.org/10.1023/A:1023486127587[Crossref]
  • [20] V.D. Kiselev, A.I. Konovalov, J. Phys. Org. Chem. 22, 466 (2009) http://dx.doi.org/10.1002/poc.1503[Crossref]
  • [21] G. Leroy, M. Sana, L.A. Burke, M.T. Nguyen, Quantum Theory Chem. React. 1, 91 (1980)
  • [22] L.R. Domingo, M.J. Aurell, P. Perez, R. Contreras, J. Org. Chem. 68, 3884 (2003) http://dx.doi.org/10.1021/jo020714n[Crossref]
  • [23] R. Jasiński, M. Kwiatkowska, A. Barański, Wiad. Chem. 61, 485 (2007)
  • [24] R.B. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry (Verlag Chemie Academic Press, Weinheim & New York, 2004)
  • [25] E.V. Anslyn, D.A. Dougherty, Modern physical organic chemistry (University Science Books, California, 2006)
  • [26] P.A. Wade, J.K. Murray Jr., S. Shah-Patel, P.J. Carroll, Tetrahedron Lett. 43, 2585 (2002) http://dx.doi.org/10.1016/S0040-4039(02)00348-9[Crossref]
  • [27] P.A. Wade, J.K. Murray Jr., S. Shah-Patel, H.T. Lee, Chem. Commun. 1090 (2002)
  • [28] D.V. Steglenko, M.E. Kletsky, S.V. Kurbatov, A.V. Tatarov, V. I. Minkin, R. Goumont, F. Terrier, J. Phys. Org. Chem. 20, 298 (2009) http://dx.doi.org/10.1002/poc.1469[Crossref]
  • [29] A. Pipic, PhD thesis (Drexel University, 2010)
  • [30] L.R. Domingo, M.J. Aurell, M.N. Kneeteman, P.M. Mancini, J. Mol. Struct. (TheoChem) 853, 68 (2008) http://dx.doi.org/10.1016/j.theochem.2007.12.004[Crossref]
  • [31] P. Arroyo, M.T. Picher, L.R. Domingo, J. Mol. Struct. (TheoChem) 709, 45(2004) http://dx.doi.org/10.1016/j.theochem.2003.10.072[Crossref]
  • [32] L.R. Domingo, A. Asensio, P. Arroyo, J. Phys. Org. Chem. 15 660, (2002) http://dx.doi.org/10.1002/poc.529[Crossref]

Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_s11532-011-0088-5
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