메뉴 건너뛰기




Volumn 7, Issue 6, 2010, Pages 432-439

Understanding the High Reactivity of the Azomethine Ylides in [3 + 2] Cycloaddition Reactions

Author keywords

2n + 2 cycloaddition; 3+2 cycloaddition; Azomethine ylides; ELF analysis; Pseudo diradicals; Reaction mechanism

Indexed keywords


EID: 78649507886     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017810791824900     Document Type: Article
Times cited : (129)

References (45)
  • 3
    • 33748936945 scopus 로고    scopus 로고
    • Potekhin, A.A.; Kostikov, R.R.; Baird, M.S. Eds.; St. Petersburg University Press: St. Petersburg
    • c) Huisgen, R.; Mloston, G. Modern Problem of Organic Chemistry. Potekhin, A.A.; Kostikov, R.R.; Baird, M.S. Eds.; St. Petersburg University Press: St. Petersburg, 2004, vol. 14, pp. 23-45.
    • (2004) Modern Problem of Organic Chemistry , vol.14 , pp. 23-45
    • Huisgen, R.1    Mloston, G.2
  • 6
    • 70349289161 scopus 로고    scopus 로고
    • Understanding the mechanism of polar Diels-Alder reactions
    • Domingo, L. R.; Sáez, J. A. Understanding the mechanism of polar Diels-Alder reactions. Org. Biomol. Chem., 2009, 7, 3576-3583.
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 3576-3583
    • Domingo, L.R.1    Sáez, J.A.2
  • 7
    • 0030018945 scopus 로고    scopus 로고
    • Density functional theory prediction of the relative energies and isotope effects for the concerted and stepwise mechanisms of the Diels-Alder reaction of butadiene and ethylene
    • a) Goldstein, E.; Beno, B.; Houk, K. N. Density functional theory prediction of the relative energies and isotope effects for the concerted and stepwise mechanisms of the Diels-Alder reaction of butadiene and ethylene. J. Am. Chem. Soc., 1996, 118, 6036-6043.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6036-6043
    • Goldstein, E.1    Beno, B.2    Houk, K.N.3
  • 8
    • 0031556561 scopus 로고    scopus 로고
    • Quantum mechanical methods and the interpretation and prediction of pericyclic reaction mechanisms
    • b) Wiest, O.; Montiel, D. C.; Houk, K. N. Quantum mechanical methods and the interpretation and prediction of pericyclic reaction mechanisms. J. Phys. Chem. A, 1997, 101, 8378-8388.
    • (1997) J. Phys. Chem. A , vol.101 , pp. 8378-8388
    • Wiest, O.1    Montiel, D.C.2    Houk, K.N.3
  • 9
    • 66749109267 scopus 로고    scopus 로고
    • An analysis of the regioselectivity on 1,3-dipolar cycloadditions of benzonitrile Noxides based on global and local electrophilicity and nucleophilicity indices
    • Domingo, L. R.; Chamorro, E.; Pérez, P. An analysis of the regioselectivity on 1,3-dipolar cycloadditions of benzonitrile Noxides based on global and local electrophilicity and nucleophilicity indices. Eur. J. Org. Chem., 2009, 3036-3044.
    • (2009) Eur. J. Org. Chem. , pp. 3036-3044
    • Domingo, L.R.1    Chamorro, E.2    Pérez, P.3
  • 10
    • 0027201157 scopus 로고
    • Electrostatic effects in 1,3-dipolar cyloaddition reactions to chiral allyl ethers: A rationale for the experientally observed diastereoselectivities
    • a) Annunziata, R.; Benaglia, M.; Cinquini, M.; Raimondi, L. Electrostatic effects in 1,3-dipolar cyloaddition reactions to chiral allyl ethers: a rationale for the experientally observed diastereoselectivities. Tetrahedron Lett., 1993, 49, 8629-8636.
    • (1993) Tetrahedron Lett. , vol.49 , pp. 8629-8636
    • Annunziata, R.1    Benaglia, M.2    Cinquini, M.3    Raimondi, L.4
  • 11
    • 37049081492 scopus 로고
    • Semiempirical molecular orbital study on the transition state for the anti-selective Michael Addition reactions of the Z-Enolates of NAlkylideneglycinates to a,b-Unsaturated Esters.
    • b) Tatsukawa, A.; Hawatake, K.; Kanemasa, S.; Rudzinski, J. M. Semiempirical molecular orbital study on the transition state for the anti-selective Michael Addition reactions of the Z-Enolates of NAlkylideneglycinates to a,b-Unsaturated Esters. J. Chem. Soc. Perkin Trans. 2, 1994, 2525-2530.
    • (1994) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 2525-2530
    • Tatsukawa, A.1    Hawatake, K.2    Kanemasa, S.3    Rudzinski, J.M.4
  • 12
    • 0001741213 scopus 로고    scopus 로고
    • Stereocontrolled synthesis of highly substituted proline esters vi [3+2] cycloaddition betwen n-metaled azomethine ylides and notroalkenes: Origin of the metal effect on the stereochemical outcome
    • c) Ayerbe, M.; Arrieta, A.; Cossío, F. P. Stereocontrolled synthesis of highly substituted proline esters vi [3+2] cycloaddition betwen n-metaled azomethine ylides and notroalkenes: origin of the metal effect on the stereochemical outcome. J. Org. Chem., 1998, 63, 1795-1805.
    • (1998) J. Org. Chem. , vol.63 , pp. 1795-1805
    • Ayerbe, M.1    Arrieta, A.2    Cossío, F.P.3
  • 13
    • 0033612308 scopus 로고    scopus 로고
    • Theoretical study of the 1,3-dipolar cycloaddition reactions of azomethine ylides. A DFT study of reaction between trifluoromethyl thiomethyl azomethine ylide and acronitrile
    • Domingo, L. R. Theoretical study of the 1,3-dipolar cycloaddition reactions of azomethine ylides. A DFT study of reaction between trifluoromethyl thiomethyl azomethine ylide and acronitrile. J. Org. Chem., 1999, 64, 3922-3929.
    • (1999) J. Org. Chem. , vol.64 , pp. 3922-3929
    • Domingo, L.R.1
  • 14
    • 17444399690 scopus 로고    scopus 로고
    • Theoretical study of the highly diastereoselective 1,3-dipolar cycloaddition of 1,4-dihydropyridine-containing azomethine ylides to 60 fullerene (Prato's reaction)
    • Alvarez, A.; Ochoa, E.; Verdecia, Y.; Suarez, M.; Sola, M.; Martin, N. Theoretical study of the highly diastereoselective 1,3-dipolar cycloaddition of 1,4-dihydropyridine-containing azomethine ylides to 60 fullerene (Prato's reaction). J. Org. Chem., 2005, 70, 3256-3262.
    • (2005) J. Org. Chem. , vol.70 , pp. 3256-3262
    • Alvarez, A.1    Ochoa, E.2    Verdecia, Y.3    Suarez, M.4    Sola, M.5    Martin, N.6
  • 16
    • 0030166214 scopus 로고    scopus 로고
    • Topological analysis of the electron localization function applied to delocalized bonds
    • b) Savin, A.; Silvi, B.; Colonna, F. Topological analysis of the electron localization function applied to delocalized bonds. Can. J. Chem., 1996, 74, 1088-1096
    • (1996) Can. J. Chem. , vol.74 , pp. 1088-1096
    • Savin, A.1    Silvi, B.2    Colonna, F.3
  • 18
    • 0037009306 scopus 로고    scopus 로고
    • The synaptic order: A key concept to understand multicenter bonding
    • d) Silvi, B. The synaptic order: a key concept to understand multicenter bonding. J. Mol. Struct., 2002, 614, 3-10.
    • (2002) J. Mol. Struct. , vol.614 , pp. 3-10
    • Silvi, B.1
  • 20
    • 0000189651 scopus 로고
    • Density-functional thermochemistry 3. the role of exact exchange
    • a) Becke, A. D. Density-functional thermochemistry 3. The role of exact exchange. J. Chem. Phys., 1993, 98, 5648-5652.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 21
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetticorrelation-energy formula into a functional of the electron density
    • b) Lee, C.; Yang, W.; Parr, R. G. Development of the Colle- Salvetticorrelation-energy formula into a functional of the electron density. Phys. Rev. B, 1988, 37, 785-789.
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 23
    • 84986439201 scopus 로고
    • Optimization of equilibrium geometries and transition structures
    • a) Schlegel, H. B. Optimization of equilibrium geometries and transition structures. J. Comput. Chem. 1982, 3, 214-218
    • (1982) J. Comput. Chem. , vol.3 , pp. 214-218
    • Schlegel, H.B.1
  • 25
    • 0004465903 scopus 로고
    • A formulation of reactions coordinate
    • Fukui, K. A formulation of reactions coordinate. J. Phys. Chem., 1970, 74, 4161-4163.
    • (1970) J. Phys. Chem. , vol.74 , pp. 4161-4163
    • Fukui, K.1
  • 26
    • 33750614386 scopus 로고
    • Reaction-path following massweighted internal coordinates
    • a) González, C.; Schlegel, H. B. Reaction-path following massweighted internal coordinates. J. Phys. Chem., 1990, 94, 5523-5527.
    • (1990) J. Phys. Chem. , vol.94 , pp. 5523-5527
    • González, C.1    Schlegel, H.B.2
  • 27
    • 36449008790 scopus 로고
    • Improved algorithms for reaction-path following-higher-order implicit algorithms
    • b) González, C.; Schlegel, H. B. Improved algorithms for reaction-path following-higher-order implicit algorithms. J. Chem. Phys., 1991, 95, 5853-5860.
    • (1991) J. Chem. Phys. , vol.95 , pp. 5853-5860
    • González, C.1    Schlegel, H.B.2
  • 29
    • 0011083499 scopus 로고
    • Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
    • b) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev., 1988, 88, 899-926.
    • (1988) Chem. Rev. , vol.88 , pp. 899-926
    • Reed, A.E.1    Curtiss, L.A.2    Weinhold, F.3
  • 30
    • 0000393496 scopus 로고    scopus 로고
    • Computational tools for the electron localization function topological analysis
    • Noury, S.; Krokidis, X.; Fuster, F.; Silvi, B. Computational tools for the electron localization function topological analysis. Comput. Chem., 1999, 23, 597-604.
    • (1999) Comput. Chem. , vol.23 , pp. 597-604
    • Noury, S.1    Krokidis, X.2    Fuster, F.3    Silvi, B.4
  • 31
    • 0027946619 scopus 로고
    • Classification of chemical-bonds based on topological analysis of electron localization functions
    • a) Silvi, B.; Savin, A. Classification of chemical-bonds based on topological analysis of electron localization functions. Nature, 1994, 371, 683-686
    • (1994) Nature , vol.371 , pp. 683-686
    • Silvi, B.1    Savin, A.2
  • 32
    • 33748225446 scopus 로고
    • Localization of electrons in intermetallic phases containing aluminum
    • Häussermann, U.; Wengert, S.; Nesper, R. Localization of electrons in intermetallic phases containing aluminum. Angew. Chem. Int. Ed. Engl., 1994, 33, 2069-2073.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2069-2073
    • Häussermann, U.1    Wengert, S.2    Nesper, R.3
  • 33
    • 37549006850 scopus 로고
    • Application of pople-santry-segal CNDO method to cyclopropylcarbinyl and cyclobutyl cation and to bicyclobutane
    • Wiberg, K. B. Application of pople-santry-segal CNDO method to cyclopropylcarbinyl and cyclobutyl cation and to bicyclobutane. Tetrahedron, 1968, 24, 1083-1096.
    • (1968) Tetrahedron , vol.24 , pp. 1083-1096
    • Wiberg, K.B.1
  • 34
    • 78650397841 scopus 로고
    • Geometry optimizations of 1,3-diradicals - ring-opened aziridine and ethylene-oxide
    • Yamaguchi, K.; Nishio, A., Yabushita, S.; Fueno, T. Geometry optimizations of 1,3-diradicals - ring-opened aziridine and ethylene-oxide. Chem. Lett., 1977, 1479-1482.
    • (1977) Chem. Lett. , pp. 1479-1482
    • Yamaguchi, K.1    Nishio Yabushita, A.S.2    Fueno, T.3
  • 36
    • 5244245983 scopus 로고
    • A correlation of reaction rates
    • Hammond, G. S. A correlation of reaction rates. J. Am. Chem. Soc., 1955, 77, 334-338.
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 334-338
    • Hammond, G.S.1
  • 37
    • 0041732169 scopus 로고    scopus 로고
    • The joint use of catastrophe theory and electron localization function to characterize molecular mechanisms. A density functional study of the Diels-Alder reaction between ethylene and 1,3-butadiene
    • a) Berski, S.; Andres, J.; Silvi, B.; Domingo, L. R. The joint use of catastrophe theory and electron localization function to characterize molecular mechanisms. A density functional study of the Diels-Alder reaction between ethylene and 1,3-butadiene. J. Phys. Chem. A, 2003, 107, 6014-6024
    • (2003) J. Phys. Chem. A , vol.107 , pp. 6014-6024
    • Berski, S.1    Andres, J.2    Silvi, B.3    Domingo, L.R.4
  • 38
    • 7044263244 scopus 로고    scopus 로고
    • Understanding the molecular mechanism of the 1,3-dipolar cycloaddition between fulminic acid and acetylene in therms of the electron localization function and catastrophe theory
    • b) Polo, V.; Andres, J.; Castillo, R.; Berski, S.; Silvi, B. Understanding the molecular mechanism of the 1,3-dipolar cycloaddition between fulminic acid and acetylene in therms of the electron localization function and catastrophe theory. Chem. Eur. J., 2004, 10, 5165-5172
    • (2004) Chem. Eur. J. , vol.10 , pp. 5165-5172
    • Polo, V.1    Andres, J.2    Castillo, R.3    Berski, S.4    Silvi, B.5
  • 39
    • 33845545242 scopus 로고    scopus 로고
    • 1,3-Dipolar cycloadditions of electrophilically activated benzonitrile N-oxides. Polar cycloaddition versus oxime formation
    • c) Domingo, L. R.; Picher, M. T.; Arroyo, P.; Saez, J. A. 1,3-Dipolar cycloadditions of electrophilically activated benzonitrile N-oxides. Polar cycloaddition versus oxime formation. J. Org. Chem., 2006, 71, 9319-9330
    • (2006) J. Org. Chem. , vol.71 , pp. 9319-9330
    • Domingo, L.R.1    Picher, M.T.2    Arroyo, P.3    Saez, J.A.4
  • 40
    • 33846434468 scopus 로고    scopus 로고
    • New finding on the Diels-Alder Reactions. An analysis based on the bonding evolution theory
    • d) Berski, S.; Andres, J.; Silvi, B.; Domingo, L. R. New finding on the Diels-Alder Reactions. An analysis based on the bonding evolution theory. J. Phys. Chem. A, 2006, 110, 13939-13947
    • (2006) J. Phys. Chem. A , vol.110 , pp. 13939-13947
    • Berski, S.1    Andres, J.2    Silvi, B.3    Domingo, L.R.4
  • 41
    • 49649122819 scopus 로고    scopus 로고
    • Understanding reaction mechanisms in organic chemistry from catastrophe theory applied to the electron localization function topology
    • e) Polo, V.; Andres, J.; Berski, S.; Domingo, L. R.; Silvi, B. Understanding reaction mechanisms in organic chemistry from catastrophe theory applied to the electron localization function topology. J. Phys. Chem. A, 2008, 112, 7128-7136
    • (2008) J. Phys. Chem. A , vol.112 , pp. 7128-7136
    • Polo, V.1    Andres, J.2    Berski, S.3    Domingo, L.R.4    Silvi, B.5
  • 42
    • 64249166380 scopus 로고    scopus 로고
    • A combined experimental and theoretical study of the polar [3+2] cycloaddition of electrophilically activated carbonyl ylides with aldehydes and imines
    • f) Bentabed-Ababsa, G.; Derdour, A.; Roisnel, T.; Sáez, J. A.; Pérez, P.; Chamorro, E.; Domingo, L. R.; Mongin, F. A combined experimental and theoretical study of the polar [3+2] cycloaddition of electrophilically activated carbonyl ylides with aldehydes and imines. J. Org. Chem., 2009, 74, 2120-2133
    • (2009) J. Org. Chem. , vol.74 , pp. 2120-2133
    • Bentabed-Ababsa, G.1    Derdour, A.2    Roisnel, T.3    Sáez, J.A.4    Pérez, P.5    Chamorro, E.6    Domingo, L.R.7    Mongin, F.8
  • 43
    • 65149090081 scopus 로고    scopus 로고
    • Understanding the regio-and chemoselective polar [3+2] cycloaddition of the Padwa carbonyl ylides with α-methylene ketones. A DFT Study
    • g) Benchouk, W.; Mekelleche, S. M.; Aurell, M. J.; Domingo, L. R. Understanding the regio-and chemoselective polar [3+2] cycloaddition of the Padwa carbonyl ylides with α-methylene ketones. A DFT Study. Tetrahedron, 2009, 65, 4644-4651.
    • (2009) Tetrahedron , vol.65 , pp. 4644-4651
    • Benchouk, W.1    Mekelleche, S.M.2    Aurell, M.J.3    Domingo, L.R.4
  • 44
    • 0000334076 scopus 로고    scopus 로고
    • Reply to comment "Electronic reorganization in 1,3-dipolar cycloaddition of fulminic acid to acetylene" J
    • Harcourt, R. D. Reply to comment "Electronic reorganization in 1,3-dipolar cycloaddition of fulminic acid to acetylene" J. Phys. Chem. A, 2001, 105, 10947-10948.
    • (2001) Phys. Chem. A , vol.105 , pp. 10947-10948
    • Harcourt, R.D.1
  • 45
    • 0141925283 scopus 로고    scopus 로고
    • 1,3-cycloaddition of ozone to ethylene, benzene, and phenol: A comparative a initio study
    • Hendrickx, M. F. A.; Vinckier, C. 1,3-cycloaddition of ozone to ethylene, benzene, and phenol: a comparative a initio study. J. Phys. Chem. A, 2003, 107, 7574-7580.
    • (2003) J. Phys. Chem. A , vol.107 , pp. 7574-7580
    • Hendrickx, M.F.A.1    Vinckier, C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.