- Adamantylation of carbonitriles with 1,3-dehydroadamantane and its homologs
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1,3-Dehydroadamantane and its methyl-substituted homologs react with carbonitriles at the α-carbon atom of the latter to give the corresponding α-adamantyl carbonitriles. This reaction provide a convenient one-step procedure for selective synthesis of branched nitriles which are difficult to obtain by traditional procedures.
- Mokhov,Butov
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- One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions
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A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.
- Ezawa, Masatoshi,Togo, Hideo
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p. 2379 - 2384
(2017/05/01)
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- Conversion of 3,3,3-Trisubstituted Prop-1-ynes with tert-Butylhydrazine into 3,3,3-Trisubstituted Propionitriles Catalyzed by TpRh(C2H4)2/P(2-furyl)3
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The combination of TpRh(C2H4)2 (Tp = tris(pyrazol-1-yl)borate) and P(2-furyl)3 catalyzes the reaction of tertiary alkyl-substituted alkynes with tert-butylhydrazine, leading to the formation of 3,3,3-trisubstituted propionitrile derivatives. This reaction system is applicable to 1,1-disubstituted propargyl alcohols and amines to afford the corresponding β-cyanohydrins and β-amino nitriles, respectively. The catalytic cycle involves the formation of a vinylidenerhodium complex as a key intermediate.
- Fukumoto, Yoshiya,Tamura, Yuto,Iyori, Yasuaki,Chatani, Naoto
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p. 3161 - 3167
(2016/05/19)
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- A facile and efficient one-pot synthesis of nitriles from carboxylic acids
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Direct transformation of aliphatic carboxylic acids to the corresponding nitriles can be easily performed with acetonitrile in the presence of sulfuric acid. Georg Thieme Verlag Stuttgart.
- Mlinari?-Majerski, Kata,Margeta, Renato,Veljkovi?, Jelena
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p. 2089 - 2091
(2007/10/03)
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