PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Czasopismo
2005 | 3 | 3 | 417-431
Tytuł artykułu

New transformation of cycloalkanone acetals by peracids α,ω-dicarboxylic acids synthesis

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A new process of oxidation of cycloalkanone acetals under the action of in situ generated performic acid has been found. The main products of the reaction are α, ω-dicarboxylic acids obtained with the yield up to 77% depending on the size of acetals ring. The process has been explored and optimized on the example of the dodecanedioic acid synthesis (a valuable industrial product).
Wydawca

Czasopismo
Rocznik
Tom
3
Numer
3
Strony
417-431
Opis fizyczny
Daty
wydano
2005-09-01
online
2005-09-01
Twórcy
  • N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky Prospect 47, Moscow, Russia, alterex@yandex.ru
  • N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky Prospect 47, Moscow, Russia
Bibliografia
  • [1] Baeyer and V. Villiger: “Einwirkung des Caro'schen Reagens auf Ketone”, Ber., V., Vol. 32, (1899), pp. 3625–3633.
  • [2] C.H. Hassell: Organic reactions, Vol. 9, Ch.3, Wiley and Sons, New York-London, 1958.
  • [3] V.N. Belov, L.A. Heifits and S.I. Varezub: Reactions and methods of research of organic compounds, Vol. 10, GCHI, Moscow, 1961.
  • [4] Methoden der Organischen Chemie (Houben-Weyl), 4th ed., Georg Thieme Verlag, Stuttgard, 1963, pp. 707.
  • [5] G.R. Krow: “Oxygen insertion reactions of bridged bicyclic ketones”, Tetrahedron, Vol. 37, (1981), pp. 2697–2724. http://dx.doi.org/10.1016/S0040-4020(01)92337-3[Crossref]
  • [6] M. Renz and B. Meunier: “100 Years of Baeyer-Villiger Oxidations”, Eur. J. Org. Chem., (1999), pp. 737–750.
  • [7] W.F. Bailey and M.-J. Shih: “Oxidation of Ketals to Orthocarbonates: A Double Baeyer-Villiger Reaction”, J. Am. Chem. Soc., Vol. 104, (1982), pp. 1769–1771. http://dx.doi.org/10.1021/ja00370a068[Crossref]
  • [8] W.F. Bailey and J.J. Bischoff: “Formation of Cyclic Ethers in the Double Baeyer-Villiger Oxidation of Ketals Derived from Cyclic Ketones”, J. Org. Chem., Vol. 50, (1985), pp. 3009–3010. http://dx.doi.org/10.1021/jo00216a045[Crossref]
  • [9] T. Sugimura, Y. Fujiwara and A. Tai: “Asymmetric Baeyer-Villiger reaction: Diastereodifferentiating peracid oxidation of chiral acetal in the presence of Lewis acid”, Tetrahedron Lett., Vol. 34, (1997), pp. 6019–6022. http://dx.doi.org/10.1016/S0040-4039(97)01338-5[Crossref]
  • [10] Y. Gaony: “Oxidation of 2,7-Dioaxabicyclo[2.2.1]heptanes with m-Chlorperbenzoic acid. 2,7,8-Trioxabicyclo[3.2.1]octanes”, J. Chem. Soc. C., Vol. 23, (1968), pp. 2934–2941. http://dx.doi.org/10.1039/j39680002934[Crossref]
  • [11] P.A. Grieco, T. Oguri and Y. Yokoyama: “One-step conversion of protected lactols into lactones”, Tetrahedron Lett., Vol. 5, (1978), pp. 419–420. http://dx.doi.org/10.1016/S0040-4039(01)91443-1[Crossref]
  • [12] D.D. Davis and D.L. Sullivan: “Process for the preparation of dodecandioic acid by oxidation of cyclododecene”, US Pat. 5026461; Chem. Abstr., Vol 115, (1991), pp. 114024.
  • [13] K. Schermanz, M. Schoeftner, E. Kloimstein, J. Schaller, E. Perndorfer, K. Reiter and R. Nehofer: “Preparation of α, ω-alkanedioic acids by ozonolysis, hydrogenation and oxidation of cycloalkenes”, Eur. Pat. Appl., EP 432541, (1991); Chem. Abstr., Vol. 115, (1991), pp. 114023.
  • [14] Standard Oil Development Co.: “Dicarboxylic acids from saturated monocarboxylic acids”, GB 706650, (1954); Chem. Abstr., Vol. 48, (1954), pp. 8818.
  • [15] Esso Research and Engineering Co.: “1,12-Dodecandioic acid”, GB 878241, (1959); Chem. Abstr., Vol. 56, (1962), pp. 8570.
  • [16] N.E. Drysdale, T.W. Stambaugh and J.V. Tarbell: “Solventless dimeric cyclic ester distillation process” US Pat. 5236560, (1993); Chem. Abstr., Vol. 119, (1993), pp. 252569.
  • [17] O. Shohachi, N. Katsuyuki and M. Yoshiyuki: “1,12-Dodecane dioic acid”, Jap. Pat. 7429164, (1974); Chem. Abstr., Vol. 82, (1975), pp. 139366.
  • [18] L. Marosi and W. Schlenk: “Langkettige Carbonsäureester: Schmelzpunkte Regeln für das Auftreten des Vertikaltyps der Kristallstruktur, Inkremente des großen Netzebenenabstandes”, Justus Liebigs Ann. Chem., (1973), pp. 584–598. [Crossref]
  • [19] R. Bhattacharaya, S.R. Saletore and J.L. Simonsen: “A synthesis of Behenolic acid”, J. Chem. Soc., (1928), pp. 2678–2681. [Crossref]
  • [20] H. Stetter and W. Dierichis: “Eine neue Methode zur Darstellung Langkettiger Carbonsäuren, II. Mitteil.*): Vereinfachtes Verfahren zur Darstellung langkettiger Carbonsäuren”, Chem. Ber., Vol. 85, (1952), pp. 290–292.
  • [21] M.D. Potter and E.P. Taylor: “The reaction of Sodiomalonic Esters with a Halogenocarboxylic Acid”, J. Chem. Soc., (1951), pp. 3513–3513.
  • [22] S. Ravi, D. Padmanabhan and V.M. Mamdapur: “Macrocyclic musk compounds: Synthetic approaches to key intermediates for exaltolide, exaltone and dilactones”, J. Indian. Inst. Sci, Vol. 81, (2001) pp. 299–312.
  • [23] 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 Lett., Vol. 44, (2003), pp. 7359–7363. http://dx.doi.org/10.1016/S0040-4039(03)01844-6[Crossref]
  • [24] A. A. Frimer: “Synthesis of α-Hydroxyacetals”, Synthesis, (1977), pp. 578–579.
  • [25] Hassner, R.H. Reuss and H.W. Pinnick: “Hydroxylation of Carbonyl Compounds via Silyl Enol Ethers”, J. Org. Chem., Vol. 40, (1975), pp. 3427–3429. http://dx.doi.org/10.1021/jo00911a027[Crossref]
  • [26] R.B. Moffett and G. Slomp, Jr.: “Reaction of Peracids with Δ20(21)-Steroid Enol Acetates”, J. Am. Chem. Soc., Vol. 76, (1954), pp. 3678–3682. http://dx.doi.org/10.1021/ja01632a032[Crossref]
  • [27] T.H. Kritchevsky and T.F. Gallagher: “Partial Synthesis of Compounds Related to Adrenal Cortical Hormones. XIV. Preparation of the Dihydroxyacetone Side Chain; 17α-Hydroxyprogesterone and “Substancese L and P””, J. Am. Chem. Soc., Vol. 74, (1951), pp. 184–189. http://dx.doi.org/10.1021/ja01145a064[Crossref]
  • [28] K. Sato, M. Aoki and R. Noyori: “A “Green” Route to Adipic Acid: Direct Oxidation of Cyclohexens with 30 Percent Hydrogen Peroxide”, Science, Vol. 281, (1998), pp. 1646–1647. http://dx.doi.org/10.1126/science.281.5383.1646[Crossref]
  • [29] P.S. Starcher and B. Phillips: “Synthesis of Lactones”, J. Am. Chem. Soc., Vol. 80, (1958), pp. 4079–4082. http://dx.doi.org/10.1021/ja01548a063[Crossref]
  • [30] 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. http://dx.doi.org/10.1016/S0040-4039(00)81758-X[Crossref]
  • [31] A. Napieraj, S. Zawadski and A. Zwierac: “New Routes to Diethyl 1-Alkenylphosphoramidates”, Tetrahedron, Vol. 56, (2000), pp. 6299–6306. http://dx.doi.org/10.1016/S0040-4020(00)00568-8[Crossref]
  • [32] G.A. Olah, S.C. Narang, D. Meidar and G.F. Salem: “Catalysis by solid superacids; 81. Improved Nafion-H2 perfluorinated resinsulfonic acid-catalyzed preparation of dimethyl acetals and ethylenedithioacetals, and hydrolysis of dimethyl acetals”, Synthesis, (1981), pp. 282–283.
  • [33] W.W. Zajaci and K.J. Byrne: “Relative Reactivities of Cycloalkanone Dimethyl Ketals to Hydrogenolysis by Dichloroaluminum Hydride”, J. Org. Chem., Vol. 35, (1970), pp. 3375–3377. http://dx.doi.org/10.1021/jo00835a041[Crossref]
  • [34] Hori, T. Hayashi and H. Midorikawa: “Synthesis with Dithiocarbamate Derivatives III. A New Route to Aldehydes”, Synthesis, (1974_, pp. 705–707.
  • [35] A.O. Terent'ev, A.V. Kutkin, M.M. Platonov, I.I. Vorontsov, M.Yu. Antipin, Yu.N. Ogibin and G.I. Nikishin: “Synthesis of peroxide compounds by the BF3-catalyzed reaction of acetals and enol ethers with H2O2”, Izv. Akad. Nauk, Ser. Khim., Vol. 3, (2004), pp. 650–656; Russ. Chem. Bull., Vol. 3, (2004), pp. 681–687 (Engl. Transl.).
  • [36] E.K. Starostin, A.A. Mazurchik, A.V. Ignatenko and G.I. Nikishin: “Synthesis of α-Haloadipic Acids from 1,2-Cyclohexanedione”, Synthesis, (1992), pp. 917–918.
  • [37] S.B. Mirviss: “Synthesis of ω-unsaturated acids”, J. Org. Chem., Vol. 54, (1989), pp. 1948–1951. http://dx.doi.org/10.1021/jo00269a038[Crossref]
  • [38] S. Muñoz, J. Mallén, A. Nakano, Z. Chen, I. Gay, L. Echegoyen and G.W. Gokel: “Ultrathin Monolayer Lipid Membranes from a New Family of Crown Ether-Based Bola-Amphiphiles”, J. Am. Chem. Soc., Vol. 115, (1993), pp. 1705–1711. http://dx.doi.org/10.1021/ja00058a014[Crossref]
  • [39] R. Ballini and G. Bosica: “α-Nitrocycloalcanones as a Source of α, ω-Dicarboxylic Acid Dimethyl Esters”, Tetrahedron, Vol. 53, (1997), pp. 16131–16138. http://dx.doi.org/10.1016/S0040-4020(97)10052-7[Crossref]
  • [40] B.A. Marples, C.G. Saint and J.R. Traynor: “Regiochemistry of Nucleophilic Opening of β-Substituted Styrene Oxides with Thiolate Anions: Model Experiments in the Synthesis of Leukotriene Analogues”, J. Chem. Soc. Perkin Trans. 1, (1986) pp. 567–574. http://dx.doi.org/10.1039/p19860000567[Crossref]
  • [41] E. Bosone, P. Farina, G. Guazzi, S. Innocenti and V. Marrotta: “New Synthesis of Methyl 7-oxoheptanoate: an Useful Intermediate for the Preparation of 2-(6-Methoxycarbonylhexyl)-cyclopent-2-en-1-one”, Synthesis, (1983), pp. 942–944.
  • [42] R. Ballini, M. Petrini and V. Polzonetti: “Amberlist A21 as New and Efficient Surface Catalyst for cleavage of 2-Nitrocycloalkanones”, Synthesis, (1992), pp. 355–357.
  • [43] A.J. Hubert: “A Novel Method for the Catalytic Partial Hydrogenation of Diolefins to Mono-olefins. Preparation of Cycloalkenes”, J. Chem Soc. C, (1967), pp. 2149–2152.
  • [44] J. Inanaga, K. Hirata, H. Saeki, T. Katsuki and M. Yamaguchi: “A Rapid Esterification by Means of Mixed Anhydride and its Application to Large-ring Lactonization”, Bull. Chem. Soc. Jpn., Vol. 52, (1979), pp. 1989–1993. http://dx.doi.org/10.1246/bcsj.52.1989[Crossref]
  • [45] K. Saotome, H. Komoto and T. Yamazaki: “The synthesis of α,ω-disubstituted higher alkanes from α,α,α,ω-tetrachloroalkanes”, Bull. Chem. Soc. Jpn., Vol. 39, (1966), pp. 480–484. http://dx.doi.org/10.1246/bcsj.39.480[Crossref]
  • [46] K.B. Wiberg and R.F. Waldron: “Lactones. 2. Enthalpies of Hydrolysis, Reduction, and Formation of the C4−C13 Monocyclic Lactones. Strain Energies and Conformations”, J. Am. Chem. Soc., Vol. 113, (1991), pp. 7697–7705. http://dx.doi.org/10.1021/ja00020a036[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_BF02479272
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.