- Direct conversion of aromatic aldehydes into benzamides via oxidation with potassium permanganate in liquid ammonia
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Oxidation of aromatic aldehydes by KMnO4 in liquid ammonia gives amides directly. The reaction proceeds satisfactorily when the aldehydes are activated by electron-withdrawing substituents on the ring.
- Antoniak, Damian,Sakowicz, Arkadiusz,Loska, Rafa?,Makosza, Mieczys?aw
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supporting information
(2015/01/08)
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- Et4NI-catalyzed amidation of aldehydes and alcohols with ammonium salts
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An efficient method for the oxidative amidation of benzylic aldehydes or alcohols with ammonium salts has been developed for the synthesis of primary amides using Et4NI as the catalyst and tert-butyl hydroperoxide as the oxidant. This amidation reaction is operationally straightforward and provides primary amides in moderate to good yields under mild conditions.
- Wang, Gao,Yu, Qing-Ying,Chen, Shan-Yong,Yu, Xiao-Qi
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p. 414 - 417
(2014/01/06)
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- Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine
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Cyanoguanidine is an inexpensive commodity chemical and it is found to be a useful reagent for the direct Friedel-Crafts carboxamidation of arenes. The reaction works best in an excess of Bronsted superacid, an observation suggesting the involvement of a superelectrophilic intermediate. Theoretical calculations indicate that the most stable diprotonated species involves protonation at the guanidine and cyano nitrogen atoms.
- Naredla, Rajasekhar Reddy,Klumpp, Douglas A.
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experimental part
p. 4779 - 4781
(2012/09/07)
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- Manganese oxide-catalyzed additive-and solvent-free aerobic oxidative synthesis of primary amides from primary amines
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Various kinds of primary amides could be synthesized through indirect aerobic oxygenation of primary amines using simple amorphous MnO2 under additive-and solvent-free conditions. The catalyst/product separation was very easy, and the retrieved MnO2 catalyst could be reused without an appreciable loss of its high catalytic performance.
- Yamaguchi, Kazuya,Wang, Ye,Mizuno, Noritaka
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supporting information; experimental part
p. 633 - 635
(2012/07/30)
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- Room-temperature debenzylation of N-benzylcarboxamides by N-bromosuccinimide
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A simple and highly efficient method has been developed with which to cleave the N-benzyl group on N-mono- or disubstituted carboxamides using N-bromosuccinimide (NBS) at room temperature. All the 31 substrates examined showed moderate to excellent deprotection yields. Our study also indicated that the debenzylation may involve an oxygen/light initiated free radical mechanism. Georg Thieme Verlag Stuttgart.
- Kuang, Liping,Zhou, Jing,Chen, Sheng,Ding, Ke
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p. 3129 - 3134
(2008/03/28)
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- Ketones to amides via a formal Beckmann rearrangement in 'one pot': A solvent-free reaction promoted by anhydrous oxalic acid. Possible analogy with the Schmidt reaction
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A variety of ketones can be directly converted into the secondary amides expected from a Beckmann rearrangement of the corresponding oximes in high yield, by heating them with hydroxylamine hydrochloride and anhydrous oxalic acid at ~100°C for 4-12 h. (Aromatic aldehydes afforded mixtures of nitrile and amide.) The transformation is apparently (kinetically) driven by the coupled decomposition of oxalic acid (to CO+CO2) via the fragmentation of an intermediate oxime mono-oxalate. However, an alternative pathway, mechanistically analogous to the Schmidt reaction, is not only equally likely but may well be general for the Beckmann rearrangement.
- Chandrasekhar, Sosale,Gopalaiah, Kovuru
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p. 7437 - 7439
(2007/10/03)
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- Beckmann rearrangement of ketoximes on solid metaboric acid: A simple and effective procedure
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When ketoximes admixed with solid metaboric acid (formed from boric acid at 100°C/0.1 Torr) are heated (~140°C/7-42 h), the corresponding amides or lactams are produced in excellent yields (62-92%) via the Beckmann reaction. Aromatic aldoximes undergo both dehydration to the nitrile as well as (non-stereospecific) rearrangement under the above conditions. The absence of solvent, and the mildness and low toxicity of boric acid, characterise the present procedure.
- Chandrasekhar, Sosale,Gopalaiah, Kovuru
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p. 2455 - 2457
(2007/10/03)
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- OsO4-mediated conversion of primary amines to nitriles
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Nitriles are very important intermediates in synthetic organic chemistry. Herein, we report our observation that certain primary amines can be converted to nitriles by trimethylamine N-oxide (TMO) under mild conditions in the presence of a catalytic amount of OsO4. Such a reaction could be used for synthetic purposes as well as for the analysis of functional group compatibility in designing reactions involving OsO4.
- Gao,Herzig,Wang
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p. 544 - 546
(2007/10/03)
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- AROMATIC RADICAL-ANIONS. XI. THE REACTION OF THE PRODUCTS OF THE REDUCTION OF 1-NAPHTHONITRILE BY POTASSIUM IN THF WITH METHYL IODIDE AND WATER
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The action of oxygen on the product of the one-electron reduction of 1-naphthonitrile by potassium in THF gives the starting nitrile an 4,4'-dicyano-1,1'-dinaphthyl, which indicates a reversible dimerization of the 1-naphthonitrile radical-anion.In accord with this conclusions, hydrolysis of these reduction product gives napthalene , 4,4'-dicyano-1,1'-dinaphthyl, 4-cyano-1,1'-dinaphthyl, while the action of CH3I gives 1-methylnapthalene, 1-cyano-1-methyl-1,2-dihydronaphthalene, and 4-cyano-4'-methyl-1,1'-dinaphtyl.
- Bil'kis, I. I.,Baganova, T. A.,Denisov, A. Yu.,Shteingarts, V. D.
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p. 1823 - 1829
(2007/10/02)
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