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2006 | 4 | 2 | 207-215
Tytuł artykułu

A new oxidation process. Transformation of gem-bishydroperoxides into esters

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A new oxidation process has been found where α,ω-dicarboxylic acid esters and ω-hydroxycarboxylic acid esters are formed on heating gem-bishydroperoxides in alcohol in the presence of BF3·Et2O. By addition of H2O2 to this reaction α,ω-dicarboxylic acid esters are formed almost selectively.
Wydawca
Czasopismo
Rocznik
Tom
4
Numer
2
Strony
207-215
Opis fizyczny
Daty
wydano
2006-06-01
online
2006-06-01
Twórcy
  • N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky Prospect 47, Moscow, Russia , terentev@ioc.ac.ru
  • N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky Prospect 47, Moscow, Russia
  • N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky Prospect 47, Moscow, Russia
Bibliografia
  • [1] K. Tsuchiya, Y. Hamada, A. Masuyama, M. Nojima, K.J. McCullough, H.-S. Kim, Y. Shibata and Y. Wataya: “Synthesis, Crystal Structure and Anti-Malarial Activity of Novel Spiro-1,2,4,5-Tetraoxacycloalkanes”, Tetrahedron Lett., Vol. 40, (1999), pp. 4077–4080. http://dx.doi.org/10.1016/S0040-4039(99)00653-X[Crossref]
  • [2] T. Ito, T. Tokuyasu, A. Masuyama, M. Nojima and K.J. McCullough: “Synthesis of novel macrocyclic peroxides by bis(sym-collidine)iodine (I) hexafluorophosphate-mediated cyclization of unsaturated hydroperoxides and unsaturated alcohols”, Tetrahedron, Vol. 59, (2003), pp. 525–536.
  • [3] Y. Nonami, T. Tokuyasu, A. Masuyama, M. Nojima, K.J. McCullough, H.-S. Kim and Y. Wataya: “Synthesis, crystal structure and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy acetals”, Tetrahedron Lett., Vol. 41, (2000), pp. 4681–4684. http://dx.doi.org/10.1016/S0040-4039(00)00688-2[Crossref]
  • [4] H.-S. Kim, K. Tsuchiya, Y. Shibata, Y. Wataya, Y. Ushigoe, A. Masuyama, M. Nojima and K. McCullough: “Synthetic methods for unsymmetrically-substituted 1,2,4,5-tetraoxanes and of 1,2,4,5,7-pentoxocanes”, J. Chem. Soc., Perkin Trans. 1, (1999), pp. 1867–1870.
  • [5] A.O. Terent’ev, A.V. Kutkin, Z.A. Starikova, M.Yu. Antipin, Yu.N. Ogibin and G.I. Nikishin: “New preparation of 1,2,4,5-Tetraoxanes”, Synthesis, (2004), pp. 2356–2366.
  • [6] C.W. Jefford and A.J.J. Boukouvalas: “Efficient preparation of 1,2,4,5-Tetroxanes from Bis(trimethylsilyl)peroxide and Carbonyl Compounds”, Synthesis, (1988), pp. 391–393.
  • [7] B.A. Šolaja, N. Terzić, G. Pocsfalvi, L. Gerena, B. Tinant, D. Opsenica and W.K. Milhous: “Mixed Steroidal 1,2,4,5-Tetraoxanes: Antimalarial and Antimycobacterial Activity”, J. Med. Chem., Vol. 45, (2002), pp. 3331–3336.
  • [8] J.L. Vennerstrom, H-N. Fu, W.Y. Ellis, A.L. Ager, J.K. Wood, S.L. Andersen, L. Gerena and W.K. Milhous: “Dispiro-1,2,4,5-tetraoxanes: A New Class of Antimalarial Peroxides”, J. Med. Chem., Vol. 35, (1992), pp. 3023–3027.
  • [9] Y. Dong, H. Matile, J. Chollet, R. Kaminsky, J.K. Wood and J.L. Vennerstrom: “Synthesis and Antimalarial Activity of 11 Dispiro-1,2,4,5-tetraoxane Analogues of WR 148999. 7,8,15,16-Tetraoxadispiro[5.2.5.2]hexadecanes Substituted at the 1 and 10 Positions with Unsaturated and Polar Functional Groups”, J. Med. Chem., Vol. 42, (1999), pp. 1477–1480. http://dx.doi.org/10.1021/jm980698f[Crossref]
  • [10] A.O. Terent’ev, A.V. Kutkin, M.M. Platonov, Y.N. Ogibin and G.I. Nikishin: “A new method for the synthesis of bishydroperoxides based on a reaction of ketals with hydrogen peroxide catalyzed by boron trifluoride complexes”, Tetrahedron Letters, Vol. 44, (2003), pp. 7359–7363.
  • [11] A.O. Terent’ev and S.V. Chodykin: “New transformation of cycloalkanone acetals by peracids α,ω - dicarboxylic acids synthesis”, Cent. Eur. J. Chem., Vol. 3, (2005), pp. 417–431. http://www.ingentaconnect.com/content/cesj/cejc/2005/00000003/00000003/art00005; http://www.citeulike.org/article/250155.
  • [12] I. Saito, R. Nagata, K. Yuba and T. Matsuura: “Synthesis of α-silyloxyhydroperoxides from the reaction of silyl enol ethers and hydrogen peroxide”, Tetrahedron Lett., Vol. 24, (1983), pp. 1737–1740.
  • [13] R. Ballini and G. Bosica: “α-Nitrocycloalkanones as a Source of α,ω-Dicarboxylic Acid Dimethyl Esters”, Tetrahedron, Vol. 53, (1997), pp. 16131–16138.
  • [14] N.M. Yoon, C.S. Pak, H.C. Brown, S. Krishnamurthy and T.P. Stocky: “Selective Reductions. XIX. The Rapid Reaction of Carboxylic Acids with Borane-Tetrahydrofurane. A Remarkably Convenient Procedure for the Selective Conversion of Carboxylic Acids to the corresponding Alcohols in the Presence of Other Functional Groups”, J. Org. Chem., Vol. 38, (1973), pp. 2786–2792. http://dx.doi.org/10.1021/jo00956a011[Crossref]
  • [15] A.I. Vogel: “Physical properties and Chemical Constitution. Part XIII. Aliphatic Carboxylic Esters”, J. Chem. Soc., (1948), pp. 624–644. [Crossref]
  • [16] A. Kumar, R.A. Gross and D. Jendrossek: “Poly(3-hydroxybutyrate)-depolymerase from Pseudomonas lemoignei: Catalysis of Esterification in Organic Media”, J. Org. Chem., Vol. 65, (2000), pp. 7800–7806.
  • [17] T. Nishiguchi, Y. Ishii and S. Fujisaki: “Selective monoesterification of dicarboxylic acids catalysed by ion-exchange resins”, J. Chem. Soc., Perkin Trans. 1, (1999), pp. 3023–3027.
  • [18] A.G. Bayer: ɛ-Hydroxycaproic acid esters, GB 774687, 1957; Chem. Abstr., Vol. 51, (1957), p. 16521.
  • [19] H. Serwy: “The freezing temperature of organic substances”, Bull. Soc. Chim. Belg., Vol. 42, (1933), pp. 483–501.
  • [20] L. Marosi and W. Schlenk: “Langkettige Carbonsäureester: Schmelzpunkte, Regeln für das Auftreten des Vertikaltypes der Kristallstruktur, Inkremente des großen Netzebenenabstandes”, Justus Liebigs Ann. Chem., (1973), pp. 584–598. [Crossref]
  • [21] M.-L. Alcaraz, L. Peng, P. Klotz and M. Goeldner: “Synthesis and Properties of Photoactivatable Phospholipid Derivatives Designed to Probe the Membrane-Associate Domains of Proteins”, J. Org. Chem., Vol. 61, (1996), pp. 192–201. http://dx.doi.org/10.1021/jo951350k[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-006-0012-6
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