Understanding the mechanisms of [3+2] cycloaddition reactions. the pseudoradical versus the zwitterionic mechanism

Tetrahedron

Volumn 70, Issue 6, 2014, Pages 1267-1273

  Domingo, Luis R ^a   Emamian, Saeed R ^b  

^a UNIVERSITY OF VALENCIA   (Spain)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ETHYLENE; SULFUR;

ARTICLE; ATOM; CYCLOADDITION; ELECTRON; ELECTROPHILICITY; ENTHALPY; HARDNESS; NUCLEOPHILICITY; PRIORITY JOURNAL;

EID: 84892834483     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.12.059     Document Type: Article

References (48)

1. W. Carruthers Some Modern Methods of Organic Synthesis 2nd ed. 1978 Cambridge University Cambridge
2. W. Carruthers Cycloaddition Reactions in Organic Synthesis 1990 Pergamon Oxford
3. L.R. Domingo, and J.A. Sáez Org. Biomol. Chem. 7 2009 3576 3583
4. D. Poppinger J. Am. Chem. Soc. 97 1975 7486 7488
5. C. Sosa, J. Andzelm, C.T. Lee, J.F. Blake, B.L. Chenard, and T.W. Butler Int. J. Quantum Chem. 49 1994 511 526
6. L.R. Domingo, E. Chamorro, and P. Perez Eur. J. Org. Chem. 2009 2009 3036 3044
7. A. Alvarez, E. Ochoa, Y. Verdecia, M. Suarez, M. Sola, and N. Martin J. Org. Chem. 70 2005 3256 3262
8. L.R. Domingo, E. Chamorro, and P. Pérez Lett. Org. Chem. 7 2010 432 439
9. L.R. Domingo J. Org. Chem. 64 1999 3922 3929
10. K.V. Gothelf, and K.A. Jorgensen Chem. Rev. 98 1998 863 910
11. D.H. Ess, and K.N. Houk J. Am. Chem. Soc. 129 2007 10646 10647
12. D.H. Ess, and K.N. Houk J. Am. Chem. Soc. 130 2008 10187 10198
13. G.S. Hammond J. Am. Chem. Soc. 77 1955 334 338
14. B. Braida, C. Walter, B. Engels, and P.C. Hiberty J. Am. Chem. Soc. 132 2010 7631 7637
15. P.C. Hiberty, J.P. Flament, and E. Noizet Chem. Phys. Lett. 189 1992 259 265
16. P.C. Hiberty, S. Humbel, C.P. Byrman, and J.H. van Lenthe J. Chem. Phys. 101 1994 5969-5976
17. P.C. Hiberty, and S. Shaik Theor. Chem. Acc. 108 2002 255 272
18. A.D. Becke, and K.E. Edgecombe J. Chem. Phys. 92 1990 5397 5403
19. A. Savin, A.D. Becke, J. Flad, R. Nesper, H. Preuss, and H.G. Vonschnering Angew. Chem., Int. Ed. Engl. 30 1991 409 412
20. B. Silvi, and A. Savin Nature 371 1994 683 686
21. A. Savin, B. Silvi, and F. Colonna Can. J. Chem. 74 1996 1088 1096
22. A. Savin, R. Nesper, S. Wengert, and T.F. Fässler Angew. Chem., Int. Ed. 36 1997 1808 1832
23. B. Silvi J. Mol. Struct. 614 2002 3 10
24. V. Polo, J. Andres, S. Berski, L.R. Domingo, and B. Silvi J. Phys. Chem. A 112 2008 7128 7136
25. S. Berski, J. Andres, B. Silvi, and L.R. Domingo J. Phys. Chem. A 107 2003 6014 6024
26. S. Berski, J. Andres, B. Silvi, and L.R. Domingo J. Phys. Chem. A 110 2006 13939 13947
27. L.R. Domingo, E. Chamorro, and P. Perez Org. Biomol. Chem. 8 2010 5495 5504
28. L.R. Domingo, and J.A. Sáez J. Org. Chem. 76 2011 373 379
29. In 1960 Errede et al. studied the high chemical reactivity of p-xylylene, which was attributed to its pseudodiradical character. They defined a pseudodiradical as a diamagnetic compound that behaves chemically as if was a diradical L.A. Errede, J.M. Hoyt, and R.S. Gregorian J. Am. Chem. Soc. 82 1960 5224 5227
30. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
31. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
32. W.J. Hehre, L. Radom, P.V.R. Schleyer, and J.A. Pople Ab Initio Molecular Orbital Theory 1986 Wiley New York, NY
33. H.B. Schlegel J. Comput. Chem. 3 1982 214 218
34. H.B. Schlegel D.R. Yarkony, Modern Electronic Structure Theory 1994 World Scientific Publishing Singapore
35. K. Fukui J. Phys. Chem. 74 1970 4161 4163
36. C. González, and H.B. Schlegel J. Phys. Chem. 94 1990 5523 5527
37. C. González, and H.B. Schlegel J. Chem. Phys. 95 1991 5853 5860
38. A.E. Reed, R.B. Weinstock, and F. Weinhold J. Chem. Phys. 83 1985 735 746
39. A.E. Reed, L.A. Curtiss, and F. Weinhold Chem. Rev. 88 1988 899 926
40. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, J.E. Peralta Jr., F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision A.01 2009 Gaussian Wallingford, CT
41. R.G. Parr, L.V. Szentpaly, and S. Liu J. Am. Chem. Soc. 121 1999 1922 1924
42. R.G. Parr, and R.G. Pearson J. Am. Chem. Soc. 105 1983 7512 7516
43. R.G. Parr, and W. Yang Density Functional Theory of Atoms and Molecules 1989 Oxford University New York, NY
44. L.R. Domingo, and P. Pérez Org. Biomol. Chem. 9 2011 7168 7175
45. W. Kohn, and L. Sham J. Phys. Rev. 140 1965 1133 1138
46. V. Bachler, G. Olbrich, F. Neese, and K. Wieghardt Inorg. Chem. 41 2002 4179 4193
47. P. Geerlings, F. De Proft, and W. Langenaeker Chem. Rev. 103 2003 1793 1873
48. D.H. Ess, G.O. Jones, and K.N. Houk Adv. Synth. Catal. 348 2006 2337 2361