95340-91-3Relevant academic research and scientific papers
Cerium or Ruthenium Catalyzed Oxidation of Alcohols to Carbonyl Compounds by Means of Sodium Bromate
Kanemoto, Shigekazu,Tomioka, Hiroki,Oshima, Koichiro,Nozaki, Hitosi
, p. 105 - 108 (1986)
Sodium bromate has been found to be effective oxidant for oxidation of alcohols in the presence of cerium or ruthenium compounds in biphase reaction.Selective oxidation of secondary alcohols was performed in the presence of primary ones using cerium(IV) ammonium nitrate (CAN) or cerium(IV) sulfate (CS) as catalyst.For instance, treatment of 1,10-undecanediol with CS/NaBrO3 provided 11-hydroxy-2-undecanone in 82percent yield.Ruthenium catalyzed biphase oxidation of alcohols with sodium bromate provided the corresponding aldehydes or ketones in good to excellent yields.
Synthesis and insecticidal activity of lactones derived from furan-2(5H)-one
Teixeira, Milena G.,Alvarenga, Elson S.,Pimentel, Mirian F.,Pican?o, Marcelo C.
, p. 2279 - 2289 (2015/11/10)
Ten 4,7-methanoisobenzofuran-1(3H)-ones were synthesized and their insecticidal activities against the insect pest Diaphania hyalinata were evaluated. The most active substances have been selected from the initial screening to find the dose to kill 50 (LD50) and 90percent (LD90) of the melonworm. Time-mortality curves of the three selected formulations at the LD90 concentration have been made against D. hyalinata. From the time-mortality curves we found that the formulation (3aR,4R,5S,6S,7S,7aS)- and (3aS,4S,5R,6R,7R,7aR)-5,6-dichlorohexahydro-4,7-methanoisobenzofuran-1(3H)-one + (3aR,4R,5R,6R,7S,7aS)- and (3aS,4S,5S,6S,7R,7aR)-5,6-dichlorohexahydro-4,7-methanoisobenzofuran-1(3H)-one has killed 50percent of the melonworm after 2 h, presenting the best knockdown effect. Bioassays against Solenopsis saevissima and Tetragonisca angustula were carried out for the lactones selected in the initial screening against D. hyalinata. The formulation (3aS,4R,5S,6S,7S,7aR)- and (3aR,4S,5R,6R,7R,7aS)-5,6-dibromohexahydro-4,7-methanoisobenzofuran-1(3H)-one + (3aS,4R,5R,6R,7S,7aR)- and (3aR,4S,5S,6S,7R,7aS)-5,6-dibromohexahydro-4,7-methanoisobenzofuran-1(3H)-one has killed 31.25 and 68.30percent of the pest natural enemy and the pollinator bee, respectively. At the same concentration this formulation killed 90percent of D. hyalinata. The selectivity in favor of the non-target organisms has rendered this formulation a position as a promising agrochemical.
Facile organocatalytic domino oxidation of diols to lactones by in situ-generated TetMe-IBX
Jhulki, Samik,Seth, Saona,Mondal, Manas,Moorthy, Jarugu Narasimha
, p. 2286 - 2293 (2014/03/21)
The domino oxidation of diols to lactones is an important transformation, and catalytic protocols that allow this conversion smoothly are scarce. Capitalizing on the established reactivity of tetramethyl-IBX (TetMe-IBX) and its in situ generation in the presence of a co-oxidant, such as oxone, we have shown that a variety of diols can be converted to the corresponding lactones in respectable yields by employing the precursor of TetMe-IBX, namely, tetramethyl-o-iodobenzoic acid (TetMe-IA), as a catalyst in 5 mol % in the presence of 2 equiv of oxone.
An efficient oxidative lactonization of 1,4-diols catalyzed by Cp*Ru(PN) complexes
Ito, Masato,Osaku, Akihide,Shiibashi, Akira,Ikariya, Takao
, p. 1821 - 1824 (2008/02/02)
An efficient oxidative lactonization of 1,4-diols in acetone is accomplished by the well-defined ruthenium catalyst, whose bifunctional nature underlies the high efficiency as well as unique chemo- and regioselectivity of the reaction which provides a rapid access to γ-butyrolactones including flavor lactones hinokinin, and muricatacin.
Indirect Electrooxidation of Alkohols and Aldehydes by Using a Double Mediatory System Consisting of RuO4/RuO2 and Cl+/Cl- Redoxes in an Aqueous-Organic Two-Phase System
Torii, Sigeru,Inokuchi, Tsutomu,Sugiura, Toyoyuki
, p. 155 - 161 (2007/10/02)
A double mediatory system consisting of RuO4/RuO2 and Cl+/Cl- redox couples has been developed for the indirect electrooxidation of alcohols and aldehydes.The reaction proceeds in the following manner: (1) oxidation of the substrate with ruthenium tetraoxide (RuO4) in the organic layer, (2) regeneration of ruthenium tetraoxide from ruthenium dioxide (RuO2) with active chlorine species (Cl2 or +), and (3) oxidation of chloride ion to + on the anode in the aqueous layer.The range of applicability of the present procedure is discussed by oxidations of (1)secondary alcohols to ketones, (2) primary alcohols and aldehydes to carboxylic acid, (3) 1,n-diols to lactones and keto acids, and (4) carbohydrate derivatives.
Enzymes in Organic Synthesis. 34. Preparations of Enantiomerically Pure Exo-and Endo-Bridged Bicyclic and Chiral Lactones via Stereospecific Horse Liver Alcohol Dehydrogenase Catalyzed Oxidations of Meso Diols
Lok, Kar P.,Jakovac, Ignac J.,Jones, J.Bryan
, p. 2521 - 2526 (2007/10/02)
Preparative-scale horse liver alcohol dehydrogenase catalyzed oxidations of saturated and unsaturated exo- and endo-bridged bicyclic and meso diols proceed with complete enantiotopic specificity to give high (64-87percent) yields of the corresponding chiral lactones of >=97percent ee.As for previous meso diol oxidations, the stereochemical course of each oxidation (S-center CH2OH oxidation in all cases) is as predicted by the cubic-space model of the active site.An illustration of the asymmetric synthetic value of these chiral lactones is provided by the conversion of one of them into a prostaglandin precursor.
CERIUM CATALYZED SELECTIVE OXIDATION OF SECONDARY ALCOHOLS IN THE PRESENCE OF PRIMARY ONES
Tomioka, Hiroki,Oshima, Koichiro,Nozaki, Hitosi
, p. 539 - 542 (2007/10/02)
The combination of (NH4)2Ce(NO3)6-NaBrO3 or Ce(SO4)2.2H2SO4-NaBrO3 has been found to be effective for the title selective oxidation.
Synthesis of the Prostaglandin H2 Analogue DL-9,11-Ethano-9,11-dideoxaprostaglandin H2
Kametani, Tetsuji,Suzuki, Toshio,Kamada, Shinko,Unno, Katsuo
, p. 3101 - 3105 (2007/10/02)
The total synthesis of the prostaglandin H2 analogue, 9,11-ethano-9,11-dideoxaprostaglandin H2 (3), starting from the known Diels-Alder adduct (4) is described.
A SIMPLE SYNTHESIS OF BICYCLOHEPTANE SYSTEM,A KEY POTENTIAL INTERMEDIATE FOR STABLE PROSTAGLANDIN H2 ANALOGUE
Suzuki, Toshio,Tomino, Akiko,Matsuda, Yasuyuki,Unno, Katsuo,Kametani Tetsuji
, p. 1735 - 1738 (2007/10/02)
A simple and efficient synthesis of 6-cyanomethyl-1-methoxycarbonylbicycloheptane system leading to stable prostaglandin H2 analogue is described.
