- Advanced Synthesis of Dihydrofurans: Effect of Formic Acid on the Mn(III)-Based Oxidation
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The Mn(III)-based oxidation of a tertiary alkylamine, such as nitrilotris(ethane-2,1-diyl) tris(3-oxobutanoate) (1) with 1,1-diphenylethene (2a), effectively proceeded in an acetic acid-formic acid mixed solvent to give nitrilotris(ethane-2,1-diyl) tris(2-methyl-5,5-diphenyl-4,5-dihydrofuran-3-carboxylate) (3). Other typical Mn(III)-based reactions of various β-diketo esters 4a-e, 2,4-pentanedione (6a), malonic acid (6b), and diethyl malonate (6c) with 1,1-diarylthenes 2a-d were also investigated in a similar acetic acid-formic acid mixed solvent and the reaction rate was accelerated and the product yield increased.
- Matsumoto, Risa,Nishino, Hiroshi
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p. 1807 - 1816
(2015/08/06)
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- Manganese(II)- and (III)-mediated Free-radical Cyclisation of Alkenes, β-Keto Esters and Molecular Oxygen
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The reactions of substituted ethenes with β-keto esters in the presence of a mixture of manganese(II) and manganese(III) acetates, and molecular oxygen yielded substituted 1,2-dioxan-3-ols 3 in 14-95percent yields.Cobalt(III) acetate, potassium permanganate, lead(IV) acetate, copper(II) acetate, chromium(VI) trioxide, thallium(III) acetate, ammonium cerium(IV) nitrate and iron(III) perchlorate were also used in place of manganese(III) acetate.Effects on the product yields of substituents in the alkenes and β-keto esters have been examined and reaction mechanisms are discussed.
- Yamada, Takashi,Iwahara, Yoko,Nishino, Hiroshi,Kurosawa, Kazu
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p. 609 - 616
(2007/10/02)
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- Formation of 1,2-dioxacyclohexanes by the reaction of alkenes with tris(2,4-pentanedionato)manganese(III) or with β-ketocarbonyl compounds in the presence of manganese(III) acetate
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The reactions of 1,1-disubstituted ethenes, styrene, 1-octene, 1-nonene, cyclohexene and cyclooctene with tris(2,4-pentanedionato)manganese(III) in acetic acid at room temperature give 4-acetyl-3-hydroxy-3-methyl-1,2-dioxacyclohexanes in 8-92% yields. The
- Tategami,Yamada,Nishino,Korp,Kurosawa
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p. 6371 - 6374
(2007/10/02)
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