Reakcje [2+3] cykloaddycji sprzężonych nitroalkenów z nitronami

Barański, A.; Jasiński, R.

Artykuł - szczegóły

Tytuł artykułu

Reakcje [2+3] cykloaddycji sprzężonych nitroalkenów z nitronami

Autorzy

Barański A. , Jasiński R.

Wybrane pełne teksty z tego czasopisma

Identyfikatory

Warianty tytułu

[2+3] cycloaddition reactions of conjugated nitroalkenes to nitrones

Języki publikacji

Abstrakty

The work is an attempt of systematizing of the literature data concerning the regio- and stereoselectivity of [2+3] cycloadditions of conjugated nitroalkenes to nitrones. In most cases these reactions are regiospecyfic leading to the corresponding 4-nitro-isoxasolidines. In the reactions with trans-b-arylnitroethylenes, trans-configuration of the substituents at C-3 and C-4 positions of the heterocyclic ring is always favored. However, in the case of trans-b-alkylnitroethylenes, usually the 3,4-cis-isomers are formed in majority. If steric effects do not affect significantly the reaction course, the observed regioselectivity can be well explained in the terms of FMO or HSBA theory. The reaction stereoselectivity is hard to predict in advance. It seems that it depends on the equilibrium between the two complementary interactions in the reaction transition state: the attractive secondary overlaps of the reactants pz-orbitals, and the repulsive steric interactions of the reactants substituents. In some cases, the possibility of (Z)-(E) isomerisation of nitrones under reaction conditions has to be taken into account. Chemical properties of the cycloadducts resulting from the presence of nitro group in the isoxazolidine ring have also been discussed.

Słowa kluczowe

reakcje chemiczne [2+3] cykloaddycja sprzężonych nitroalkenów z nitronami regioselektywność reakcji stereoselektywność reakcji

[2+3] cycloaddition reaction stereoselectivity reaction regioselectivity

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2002

Tom

[Z] 56, 9-10

Strony

829--854

Opis fizyczny

tab., wykr., bibliogr. 53 poz.

Twórcy

autor

Barański A.

autor

Jasiński R.

Wydział Inżynierii i Technologii Chemicznej Politechniki Krakowskiej ul. Warszawska 24, 31-155 Kraków

Bibliografia

[1] J. H. Boyer, Nitro azoles : the C-Nitro Derivates of N-and NO-Five-membered Heterocycles, VCH, Berlin 1986.
[2] A. Barański, V.I. Kelarev, Khim. Geterotsikl. Soed., 1990, 435.
[3] P. Grunanger, P. Vita-Finzi , [in:] The Chemistry of Heterocyclic Compounds , vol. 49, part. 1, Wiley, New York 1991.
[4] P.N. Confalone, E.M. Huie, Organic Reactions, 1988, 36, 46.
[5] M. Frederickson, Tetrahedron, 1997, 53, 403.
[6] L.A. Motoina, L.A. Sviridova, Khim. Geterotsikl. Soed., 1992, 829.
[7] J.J. Tuffariello, [in:] 1 ,3 Dipolar Cycloaddition Chemistry , vol. 2, A. Padwa (Ed), J. Wiley & Sons, New York 1984.
[8] L. Fišera, V. Ondrus, J. Kuban, P. Micuch, I. Blanarikova, J. Heterocycl. Chem., 2000, 37, 551.
[9] D. Seebach, E.W. Colvin, F. Lehr, T. Weller, Chinia, 1979, 33, 1.
[10] G. Rosini, R. Baiini., Synthesis, 1988, 833.
[11] R. Huisgen [in:] 1-3 Dipolar Cycloaddition Chemistry, vol.1, A. Padwa (Ed), 3. Wiley & Sons, New York 1984.
[12] C. Bełżecki, I. Panfil, J. Org. Chem., 1979, 44, 1212.
[13] A.Vasella, Helv. Chim. Acta, 1977, 60, 426.
[14] I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, Chichester 1976.
[15] W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon Press, New York 1991.
[16] E. Breuer, [in:] Nitrones, nitronates, and nitroxides, E. Breuer, H.G. Aurich, A. Nielsen, (Eds); J.Wiley & Sons, Chichester 1989.
[17] T. Yakura, M. Nakazawa, T. Takino, M. Ikeda, Chem. Pharm. Bull., 1992, 40, 2014.
[18] J. Sims, K.N. Houk, J. Am. Chem. Soc., 1973, 95, 5798.
[19] K.N. Houk, A. Bimanand, D. Mukherjee, J. Sims, Ch. Yau-Ming, D.C. Kaufman, L.N. Domelsmith, Heterocycles, 1977, 7, 293.
[20] F.P. Cossio, I. Morao, H. Jiao, P. von Rague-Schleyer, J. Am. Chem. Soc., 1999, 121, 6737.
[21] A. Padwa, L. Fisera, K.F. Koehler, A. Rodriguez, J. Org. Chem., 1984, 49, 276.
[22] M. Burdisso, R. Gandolfi, P. Griinanger, Tetrahedron, 1989, 45, 5579.
[23] A. Barański, R. Jasiński, A. Markowska, [in:] Abstract of papers of V-th International Conference Theoretical and Experimental Backgrounds of Development of New High Performing Chemical Technologies and Equipment,Ivanovo (Russia) 2001, p. 118.
[24] M. Burdisso, A. Ganba, R. Gandolfi, P. Pevarello, Tetrahedron, 1987, 43, 1835.
[25] K. Tanaka, T. Mori, K. Mitsuhashi, Bull. Chem. Soc. Japan, 1993, 66, 263.
[26] M. Meske, J. Prakt. Chem., 1997,339, 426.
[27] A. Barański, Polish J. Chem., 2000, 74, 767.
[28] M. Joucla, Tetrahedron, 1973, 29, 2315.
[29] A. Barański, Polish J. Chem., 1999, 73, 1711.
[30] W. Taborski, A. Barański, [in:] Abstract of papers of VII-th International Conference The Problems of Solvation and Complex Formation in Solutions, Moscow 1998, p. 367.
[31] A. Barański, Khim. Geterotsikl. Soed., 2000, 840.
[32] A. Barański, R. Jasiński, Khim. Geterotsikl. Soed., 2001,1670.
[33] A. Barański, M. Olszańska, M. Barańska, J. Phys. Org. Chem., 2000, 13, 489.
[34] A. Barański, Khim. & Khim. Tekhnol., 1999, 42, 18.
[35] A. Barański, J. Phys. Org. Chem., 2002, 15,78.
[36] A. Padwa, K.F. Koehler, A. Rodriguez, J. Am. Chem. Soc., 1981, 103, 4974.
[37] S. Baskaran, C. Baskaran, P.J. Nadkami, G.K. Trivedi, Tetrahedron, 1997, 53, 7057.
[38] P. Borrachero, F. Cabrera, J. Dianez, D. Estrada, M. Gomez-Guillen, J.M. Moreno, J.L. de Paz, S. Perez-Garrido, Tetrahedron Asym., 1999, 10, 77.
[39] L. Fišera, U.A.R. Al.-Timari, P. Ertl, [in:] Cycloadditions in Carbohydrate Chemistry, R.M. Giuliano (Ed), ACS Monograph, Washington 1992, p. 152.
[40] V. Ramamoorthy, C. Meenakshi, S. Muthusubramanian, S. Sivasubramanian, J. Incl. Phen. and Macrocyclic Chem., 2000, 36, 425.
[41] A. Barański, R. Jasiński, M. Bujak, Polish J. Chem., 2002, 76, 145.
[42] R. Jasiński, A. Barański, Czasopismo Techn. PK (Chemia), 2001, 1.
[43] R. Sustmann, Tetrahedron Lett., 1971, 2717, 2721.
[44] E.G. Klopman, Chemical Reactivity and Reaction Paths , Wiley, New York 1972.
[45] J. Takeuchi, F. Furusaki, Adv. Eeterocycl. Chem., 1977, 21, 207.
[46] K.V. Gothelf, K.A. Jorgensen, Chem. Rev., 1998, 98, 863.
[47] A. Barański, [in:] Abstract of papers of XII-th International Conference Reaktiv-9 9, Moscow 1999, p. 222.
[48] A. Padwa, K.F. Koehler, A. Rodriguez, J. Org. Chem., 1984, 49, 282.
[49] A. Barański, V.I. Kelarev, Khim. Prirod. Soed., 1992, 291.
[50] S.C. Denmark, A. Thorarensen, Chem. Rev., 1996, 96, 137.
[52] V.V. Perekalin, E.S. Lipina, V. M. Berestovtskaya, D.A. Efremov, Nitroalkenes : Conjugated Nitrocompounds, Wiley, New York 1994.
[53] R.S. Varma, G.W. Kabalka, Heterocycles, 1986, 24, 2645.

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUS1-0010-0085