- 2,4,4,6-Tetrabromocyclohexa-2,5-dienone in the presence of triphenylphosphine as a specific reagent for nucleophilic substitution in cyanohydrins
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A convenient method for the synthesis of α-bromonitriles from aliphatic cyanohydrins using the 2,4,4,6-tetrabromocyclohexa-2,5-dienone complex with triphenylphosphine was developed.
- Matveeva, Elena D.,Podrugina, Tatyana A.,Tishkovskaya, Elena V.,Zefirov, Nikolai S.
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p. 260 - 261
(2007/10/03)
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- Oxidative Decyanation of Secondary Nitriles to Ketones
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Procedures for the oxidative decyanation of secondary nitriles to ketones involve (1) iodination of N-(trialkylsilyl)ketenimines derived from secondary nitriles and subsequent hydrolysis of the α-iodo nitriles with silver oxide, (2) addition of nitrosobenzene to N-(trialkylsilyl)ketenimines, (3) conversion of secondary nitriles to α-(phenylthio) nitriles and subsequent hydrolysis with N-bromosuccinimide in aqueous acetonitrile, and (4) preparation of α-hydroperoxy nitriles by direct oxygenation of anions of secondary nitriles and subsequent reductive hydrolysis with stannous chloride followed by sodium hydroxide.The latter general procedure was applied to various secondary nitriles bearing dialkyl, aryl and alkyl, and diaryl substituents to provide ketones in good yield and was extended to the oxidative decyanation of α,β-unsaturated nitriles to furnish α,β-unsaturated ketones.
- Freerksen, Robert W.,Selikson, Sandra J.,Wroble, Randall R.,Kyler, S. Keith,Watt, David S.
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p. 4087 - 4096
(2007/10/02)
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- Preparation of halogenated nitriles
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A process is disclosed for preparing halogenated hydrocarbyl nitriles comprising reacting a metal or ammonium cyanide with a dihalogenated aliphatic or alicyclic hydrocarbon of the formula X--R--CH2 --X1 where X and X1 are chloro, bromo or iodo and R is a divalent aliphatic, alicyclic or aralkyl hydrocarbon group, In an aqueous medium in the presence of a phase transfer catalyst.
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