- A facile one-pot conversion of aldehydes into nitriles
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A facile one-pot synthesis of nitriles starting with aldehydes has been developed employing hydroxylamine hydrochloride in dimethylsulfoxide at 100C.
- Chill, Samuel T.,Mebane, Robert C.
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scheme or table
p. 3601 - 3606
(2009/12/04)
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- Quantitative α-alkylation of primary nitriles
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A synthetic pathway that produces alkyl α,ω-cyanodiolefins in quantitative yield is described, applying chemistry that is based on simple α-alkylation of alkyl nitriles. Three amide bases, lithium 2,2,6,6-tetramethylpiperidide, lithium diisopropylamide, and sodium amide, are used to create the α-carbanions that undergo substitution with various alkylating agents. Optimization leads to essentially quantitative conversions for every substrate/example reported herein, which will prove useful in many synthetic schemes. Copyright Taylor & Francis Group, LLC.
- Rojas, Giovanni,Baughman, Travis W.,Wagener, Kenneth B.
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p. 3923 - 3931
(2008/03/14)
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- Highly Convenient, One-Pot Synthesis of Nitriles from Aldehydes Using the NH2OH·HCl/NaI/MeCN System
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Direct transformation of both aliphatic and aromatic aldehydes to the corresponding nitriles, can be easily performed by the reaction of an aldehyde with a slight excess of hydroxylamine hydrochloride, in refluxing acetonitrile and in the presence of 0.5 equivalents of sodium iodide as catalyst.
- Ballini, Roberto,Fiorini, Dennis,Palmieri, Alessandro
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p. 1841 - 1843
(2007/10/03)
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- Hydrogen peroxide oxidation of N,N-dimethylhydrazones promoted by selenium compounds, titanosilicalites or acetonitrile
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Hydrogen peroxide oxidation of N,N-dimethylhydrazones 1 promoted by title reagents has been investigated. Depending on the substrate nitrile 2 and/or amide 3 accompanied with carboxylic acid 4 and parent carbonyl compounds 5 were obtained. Formation of nitriles 2 with H2O2-acetonitrile system is limited for a few more active substrates. The mechanism of the reaction, based on generated in situ peroxyiminoacetic acid, is presented. A broad spectrum of aliphatic, unsaturated and aromatic nitriles 2 was obtained by oxidation of corresponding N,N-dimethylhydrazones 1 with hydrogen peroxide in the presence of poly(bis-9,10-anthracenyl) diselenide (PADS) (7) as catalyst.
- Giurg,Mlochowski,Ambrozak
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p. 1713 - 1720
(2007/10/03)
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- Methylation of organic compounds
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Methyl compounds are prepared from carbon acids by reaction with dimethyl carbonate in the presence of a nitrogen-containing base.
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- Substituent Effects on the C-C-Bond Strength, 2. The Thermal Stability of Tetrasubstituted Succinonitriles
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Rate constants and activation parameters for the thermolysis reaction of ten, partly cyclic tetraalkylsuccinonitriles and of meso-2,3-dimethyl-2,3-diphenylsuccinonitrile were determined.Relationships between ΔG* (300 deg C), ΔH* and ΔS* of the thermolysis reaction on the one hand and the change in strain enthalpy during bond dissociation on the other are pointed out.A force field procedure for the estimation of the strain in α-cyanoalkyl radicals is presented.A quantitative separation of the steric and resonance effects responsible for the thermal dissociation pro cess was achieved successfully.A resonance energy of 5.3 kcal*mol-1 was deduced for tertiary α-cyanoalkyl radicals in agreement with the most recent literature data.
- Barbe, Werner,Beckhaus, Hans-Dieter,Ruechardt, Christoph
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p. 1042 - 1057
(2007/10/02)
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