Powiadomienia systemowe
- Sesja wygasła!
- Sesja wygasła!
- Sesja wygasła!
Tytuł artykułu
Autorzy
Wybrane pełne teksty z tego czasopisma
Identyfikatory
Warianty tytułu
Mechanistic aspects of (4+2)[pi]-non-concerted cycloadditions
Języki publikacji
Abstrakty
In this work the reported in literature (4+2)[pi]-electron cycloadditions, where a two-step mechanism was postulated and more or less thoroughly documented, has been subjected to a critical analysis. The research has been focused on [2+3] and [2+4] cycloadditions. To-date not many detailed studies, which would lead to unambiguous conclusions have been performed in this area. The two-step reaction mechanism of thiocarbonylylides with 1,2-dicyanoethene derivatives, [pi]-deficient cyclic ylides with 1-(dimethylamino)-propyne and 1,1-dimethoxy-1,3-butadiene with [pi]-deficient ethene derivatives can be considered as the most documented ones. On the other hand, the reports where a non-concerted mechanism of [2+3] cycloaddition of nitrile oxides with dideuteroethenes and [2+4] cycloaddition of 2-methylfurane with 1,2-dicarboxyethene was postulated are less reliable.
Wydawca
Czasopismo
Rocznik
Tom
Strony
485--514
Opis fizyczny
bibliogr. 119 poz., tab., wykr.
Twórcy
autor
autor
autor
- Instytut Chemii i Technologii Organicznej, Politechnika Krakowska, ul. Warszawska 24, 31-155 Kraków, radomir@chemia.pk.edu.pl
Bibliografia
- [1] R. Huisgen, Angew. Chem. Int. Ed. Engl., 1963, 2, 633.
- [2] R. Huisgen, J. Org. Chem., 1968, 33, 2291.
- [3] M.J.S. Dewar, J. Am. Chem. Soc., 1984, 106, 209 i odnośniki tam cytowane.
- [4] R.A. Firestone, J. Chem. Soc. A, 1970, 1570.
- [5] R.A. Firestone, J. Org. Chem., 1972, 37, 2181.
- [6] R. Huisgen, J. Org. Chem., 1976, 41, 403.
- [7] K.N. Houk, J. Am. Chem. Soc., 1977, 99, 511.
- [8] J.J. Sauer, R. Sustmann, Angew. Chem., Int. Ed. Engl., 1980, 19, 779.
- [9] R. Huisgen [w:] 1,3-Dipolar Cycloaddition Chemistry, Ed. Padwa E., Wiley Interscience, New York 1984, t. I, r. 1.
- [10] R. Huisgen, [w:] Advances in Cycloaddition, vol. 1, JAI Press 1988.
- [11] R.A. Firestone, Tetrahedron, 1999, 55, 14459.
- [12] D.A. Singleton, B.E. Schulmeier, C. Hang, A.A. Thomas, S.-W. Laung, S.R. Merrigan, Tetrahedron, 2001, 57, 5149.
- [13] F. Fringuelli, A. Taticchi, The Diels-Alder Reaction: Selected Practical Methods, Wiley: West Sussex, Eng., 2002.
- [14] R. Huisgen, G. Mloston [w:] Modern Problem of Organic Chemistry, 2004, 14, 23.
- [15] R. Jasiński, A. Lyubimcev, A. Ciężkowska, A. Barański, Izv. VUZ (Khim. Khim. Tekh.), 2004, 47, 136.
- [16] A.S. Onishchenko, Dienovyi sintez, Izdatelstvo AN SSSR, Moskwa 1963.
- [17] A Wasserman, Diels-Aldes Reactions . Organic Backgrounds and Physico-Chemical Aspects, Elsevier 1965.
- [18] R. Huisgen, Pure Appl. Chem., 1980, 52, 2283.
- [19] A. Barański, Polish J. Chem., 1989, 63, 483.
- [20] W.J. Orville-Thomas, Internal rotation in molecules, Wiley, London 1974.
- [21] S.G. Entelis, Reaction kinetics in the liquid phase, Wiley 1976.
- [22] K. Schwietlick, Kinetische Metoden zur Untersuchung von Reaktionsmechanismen, VEB Deutscher Verlag der Wissenschaften, Berlin 1971.
- [23] Yu. Ya. Fialkov, Rastvoritiel kak sredstvo upravlenia khimicheskim processom, Khimya, Leningrad 1990.
- [24] R. Jasinski, A. Baranski, Polish J. Chem., 2006, 80, 1493.
- [25] M. Kwiatkowska, R. Jasiński, A. Barański, Czasopismo Techn. PK (Chemia), 2006, 4Ch, 95.
- [26] R. Jasiński, A. Barański, Khim. Geteroskl. Soed., 2006, 1545.
- [27] A. Baranski, R. Jasinski, K. Zurowski, J. Phys. Org. Chem., 2003, 16, 279.
- [28] K.N. Houk, R.A. Firestone, L.L. Munchausen, P.H. Mueller, B.H. Arison, L.A. Garcia, J. Am. Chem. Soc., 1985, 107, 7227.
- [29] P. Caramella, P. Grünanger [w:] 1,3-Dipolar Cycloaddition Chemistry, Ed. Padwa E., Wiley Interscience, New York 1984, t. I, r. 3.
- [30] L. Melander, W.H. Saunders, Jr., Reaction Rates of Isotopic Molecules, J.Wiley & Sons, New York, 1980
- [31] S. Morrocchi, A. Ricca, A. Zanarotti, G. Bianchi, R. Gandolfi, P. Grünanger, Tetrahedron Lett., 1969, 3329.
- [32] S. Morrocchi A. Ricca, A. Zanarotti, Lincei Rend. Sc. Fis. Mat. e Nat., 1970, 48, 231.
- [33] A. Battaglia, A., Dondoni, Tetrahedron Lett., 1970, 1221
- [34] P. Beltrame, P. Sartirana, C. Vitani, J. Chem. Soc. B, 1971, 814.
- [35] A. Dondoni, G. Barbaro, J. Chem. Soc. Perkin Trans. II, 1974, 1591.
- [36] S. Morrocchi, A. Ricca, A. Zanarotti, Tetrahedron Lett., 1970, 3215.
- [37] J. Baran, H. Mayr, J. Am. Chem. Soc., 1987, 109, 6519.
- [38] R.B.Woodward, R.Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie: Weinheim, FRG, 1971.
- [39] J. Baran, H. Mayr, J. Org. Chem., 1989, 54, 5774.
- [40] H. Mayr, J. Baran, U.W. Heigl, Gazz. Chim. Ital., 1991, 121, 373.
- [41] R. Huisgen, G. Mloston, A. Probstl , Heteroatom Chem., 2001, 12, 136.
- [42] R. Sustmann, W. Sicking, R. Huisgen, J. Am. Chem. Soc., 2003, 125, 14425.
- [43] R. Sustmann, W. Sicking, R. Huisgen, Eur. J. Org. Chem., 2005, 1505.
- [44] R. Huisgen, X. Li, G. Mloston, C. Fulka, Eur. J. Org. Chem., 2000, 1695.
- [45] R. Huisgen, G. Mloston, H. Giera, E. Langhals, K. Polborn, R. Sustmann, Eur. J. Org. Chem., 2005, 1519.
- [46] R. Huisgen, L. Mobius, G. Szeimies, Ber., 1965, 98, 1138.
- [47] R. Huisgen, G. Szeimies, Ber., 1965, 98, 1153.
- [48] R. Huisgen, G. Szeimies, L. Mobius, Ber., 1967, 100, 2494.
- [49] F.A. Gabitov, A.L. Fridman, A.D. Nikolayeva, Zh. Org. Khim., 1969, 5, 2245.
- [50] A.L. Fridman, F.A. Gabitov, Patent ZSRR 348570; C.A. 1973, 78, 29752.
- [51] F.A. Gabitov, A.L. Fridman, W.D. Surkov, Zh. Org. Khim., 1972, 8, 2457.
- [52] A. Barański, W.I. Kelarev, Khim. Geteroskl. Soed., 1990, 435 i prace cytowane tam.
- [53] R. Huisgen , E. Langhals, G. Mloston, T. Oshima, J. Rapp, J. Heterocyclic Chem., 1987, 24, S-1.
- [54] R. Huisgen, G. Mloston, E. Langhals, J. Am. Chem. Soc., 1986, 108, 6401.
- [55] R. Huisgen, G. Mloston, E. Langhals, J. Org. Chem., 1986, 51, 4085.
- [56] R. Huisgen, G. Mloston, H. Giera, E. Langhals, Tetrahedron, 2002, 58, 507.
- [57] G. Mloston, R. Huisgen, H. Giera., Tetrahedron, 2002, 58, 4185.
- [58] R. Huisgen, G. Mloston, E. Langhals, Helv. Chim. Acta., 2001, 84, 1805.
- [59] R. Huisgen, E. Langhals, G. Mloston, T. Oshima, Heterocycles, 1999, 29, 2069.
- [60] R. Huisgen, H. Giera, G. Mloston G., Tetrahedron, 2005, 61, 6143.
- [61] G. Mloston, E. Lahghals, R. Huisgen, Tetrahedron Lett., 1989, 30, 5373.
- [62] R. Huisgen, E. Langhals, J. Org. Chem., 1990, 55, 1412.
- [63] R. Huisgen, J. Penelle, G. Mloston, A.B. Padias, H.K. Hall, J. Am. Chem. Soc., 1992, 114, 266.
- [64] L.P. Domingo, T. Picher, Tetrahedron, 2004, 60, 5053.
- [65] S. Yamago, S. Ejiri, M. Nakamura, E. Nakamura. J. Am. Chem. Soc., 1993, 115, 5344.
- [66] T. Böhm , A. Weber, J. Sauer , Tetrahedron, 1999, 55, 9535.
- [67] K. Elender, P. Riebel, A. Weber, J. Sauer, Tetrahedron, 2000, 56, 4261.
- [68] H. Quast, D. Regnat, E-M. Peters, K. Peters, H.G. von Schnering, Angew. Chem. Int. Ed. Engl., 1990, 29, 695.
- [69] H. Quast, M. Ach, S. Ivanova, E-M. Peters, K. Peters, H.G. von Schnering, Liebigs Ann. Chem., 1996, 1551.
- [70] V.O. Rodionov, V.V. Fokin, M.G. Finn, Angew. Chem. Int. Ed., 2005, 44, 2210.
- [71] G. Homo, T. Lovell, R. Hilgraf, V.V. Rostovtsev, V.V Fokin, L. Noodlean, K.B., Sharpless, J. Am. Chem. Soc., 2005, 127, 210.
- [72] X. Yan, Q. Peng. Y. Zhang, K. Zhang, W. Hong, Z. Hou, Y. Wu, Angew. Chem., 2006, 118, 2013.
- [73] S. Kobayashi, K.A. Jorgensen, Cycloaddition Reaction in Organic Synthesis, Wiley, Weinheim 2002.
- [74] L.A. Telen, R.A. Firestone, Tetrahedron, 1999, 55, 14269.
- [75] R. Sustmann, H. Troll, Tetrahedron Lett., 1972, 4271
- [76] W.F. Travien, Elektronnaja struktura i swoistva organicheskikh molekuł, Moskwa, Chimija 1998.
- [77] L.M. Stephenson, R.V. Gammer, S. Current, J. Am. Chem. Soc., 1975, 97, 5909.
- [78] J.A. Berson, P.B. Dewon, R. Malherbe, J.A. Jenkins, J. Am. Chem. Soc., 1976, 98, 5937.
- [79] J.A. Berson, R. Malherbe, J. Am. Chem. Soc., 1975, 97, 5910.
- [80] V. Mark, J. Org. Chem., 1974, 39, 3179.
- [81] R. A. Firestone, Heterocycles, 1987, 25, 61
- [82] K. Mikami, S, Matsumoto, Y. Okubo, M. Fujitsuka, O. Ito, T. Suenobu, S. Fukuzumi, J. Am. Chem. Soc., 2000, 122, 2236
- [83] P.D. Bartlett, G.E.H. Wallbillich, L.K. Montgomery, J. Org. Chem., 1967, 32, 1290.
- [84] P.D. Bartlett, G.E.H. Wallbillich, A.S. Wingrove, J.S. Swenton, L.K. Mongomery, B.D. Kramer, J. Am. Chem. Soc., 1968, 90, 2049.
- [85] P.D. Barlett, Science, 1968, 159, 833.
- [86] A. Buchachenko, A.M. Wasserman, Stabilnye radikaly, Khimya, Moskwa 1973.
- [87] O.A., Reutov, A.L. Kurtz, K.P. Butin, Organiczeskaja Khimya, t. 4, s. 250, BINOM, Moskwa 2004.
- [88] P. D. Bartlett, The Chemical Society, Quart. Rev., 1970, 4, 473.
- [89] J. Little, J. Am. Chem. Soc., 1965, 87, 4020.
- [90] C. Ochoa, E. Ortuno, R. Ortuno, Tetrahedron Lett., 1995, 36, 749.
- [91] Jin F., Xu Y., Huang W., J. Fluorine Chem., 1995, 71, 1
- [92] C.A.Jr. Stewart, J. Am. Chem. Soc., 1971, 93, 4815.
- [93] C.A.Jr. Stewart, J. Am. Chem. Soc., 1972, 94, 635.
- [94] P.D. Bartlett, L.K. Montgomery, B. Seidel, J. Am. Chem. Soc., 1964, 86, 616.
- [95] R. Wheland, P.D. Bartlett, J. Am. Chem. Soc., 1970, 92, 3822.
- [96] P.D. Bartlett, J.J-B. Mallet, J. Am. Chem. Soc., 1976, 98, 143.
- [97] F.-G. Klarner, B. Krawczyk, V. Ruster, U.K. Deiters, J. Am. Chem. Soc., 1994, 116, 7646.
- [98] F.-G. Klärner, B.M. Dogan, M.J. Ermer, W. von E. Doering, M.P. Cohen, Angew. Chem., 1986, 98, 109.
- [99] F.-G. Klärner, B.M. Dogan, M.J. Ermer, W.von E.Doering, M.P. Cohen, Angew. Chem., Int. Ed. Engl., 1986, 25, 108.
- [100] R. Gompper, Angew. Chem., Int. Ed. Engl., 1969, 8, 312.
- [101] P.A. Wade, J.K. Murray Jr., S. Shah-Patel, H.T. Le, Chem. Commun., 2002, 1090.
- [102] S. Denmark, A. Thorarensen, Chem. Rev., 1996, 96, 137.
- [103] R.A.Y. Jones, Fizyczna chemia organiczna, mechanizmy reakcji chemicznych, PWN Warszawa 1988.
- [104] R. Sustmann, S. Tappanchai, H. Bandmann, J. Am. Chem. Soc., 1996, 118, 12555.
- [105] C.A.Jr. Stewart, J. Am. Chem Soc., 1962, 84, 117.
- [106] C.A.Jr. Stewart, J. Org. Chem., 1963, 28, 3320.
- [107] F. Kataoka, N. Shimizu, S. Nishida, J. Am. Chem. Soc., 1980, 102, 711.
- [108] M. Kinoshita, H. Yanagisawa, S. Doi, E. Kaji, S.Umezawa, Bull. Chem. Soc. Jpn., 1969, 42, 194
- [109] R. Sustmann, M. Rogge, U. Nuchter, H. Bandmann, Chem. Ber., 1992, 125, 1656.
- [110] R. Sustmann, M. Rogge, U. Nuchter, J. Harvey, Chem. Ber., 1992, 123, 1665.
- [111] R. Sustmann, K. Lucking, G. Kopp, M. Rese, Angew. Chem., 1989, 101, 1701.
- [112] R. Sustmann, K. Lucking, G. Kopp, M. Rese, Angew. Chem., Int. Ed. Engl., 1989, 28, 1713.
- [113] E.M. Clennan, K.K. Lewis, J. Am. Chem. Soc., 1987, 109, 2475.
- [114] E.M. Clennan, A.D. Earlywine, J. Am. Chem. Soc., 1987, 109, 7104.
- [115] F. Jensen, C.F., Foote, J. Am. Chem. Soc., 1987, 109, 6376.
- [116] G. Vassilikogiannakis i M. Orfanopoulos, Tetrahedron Lett., 1998, 39, 8891.
- [117] A. Barański, J. Mol. Struct. (TheoChem), 2000, 499, 185.
- [118] R. Jasiński, E. Brandel, A.Barański, Polish J. Chem., 2004, 78, 83.
- [119] M. Bujak, A. Barański, Czasopismo Techn. PK (Chemia), 2004, 1Ch, 13.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUS5-0004-0041