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

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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. R. Ballini and G. Bosica: “α-Nitrocycloalkanones as a Source of α,ω-Dicarboxylic Acid Dimethyl Esters”, Tetrahedron, Vol. 53, (1997), pp. 16131–16138. 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. A.I. Vogel: “Physical properties and Chemical Constitution. Part XIII. Aliphatic Carboxylic Esters”, J. Chem. Soc., (1948), pp. 624–644. 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. 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. A.G. Bayer: ɛ-Hydroxycaproic acid esters, GB 774687, 1957; Chem. Abstr., Vol. 51, (1957), p. 16521. H. Serwy: “The freezing temperature of organic substances”, Bull. Soc. Chim. Belg., Vol. 42, (1933), pp. 483–501. 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. 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.