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

• Autorzy: Alexander Terent'ev , Sergey Chodykin
• 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).

Słowa kluczowe

EN

Cycloalkanone acetals   hydrogen peroxide   dodecanedioic acid   dicarboxylic acid   performic acid   enol-ether   oxidation   Baeyer-Villiger rearrangement  

• Czasopismo: Open Chemistry
• Rocznik: 2005
• Tom: 3
• Numer: 3
• Strony: 417-431

Daty

wydano

2005-09-01

online

2005-09-01

Twórcy

autor

Alexander Terent'ev

• N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky Prospect 47, Moscow, Russia,

autor

Sergey Chodykin

• 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]

Identyfikatory

DOI

10.2478/BF02479272