- 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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- Palladium-catalyzed reactions of enol ethers: Access to enals, furans, and dihydrofurans
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The palladium-catalyzed oxidation of alkyl enol ethers to enals, which employs low loadings of a palladium catalyst, is described. The mild oxidation conditions tolerate a diverse array of functional groups, while allowing the formation of di-, tri-, and tetrasubtituted olefins. The application of this methodology to intramolecular reactions of alkyl enol ethers containing pendant alcohols provides furan and 2,5-dihydrofuran products.
- Lauer, Matthew G.,Henderson, William H.,Awad, Amneh,Stambuli, James P.
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supporting information
p. 6000 - 6003
(2013/02/25)
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- Electron transfer-induced four-membered cyclic intermediate formation: Olefin cross-coupling vs. olefin cross-metathesis
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An electron transfer-induced four-membered cyclic intermediate, formed between a radical cation of an enol ether and an unactivated olefin, played a key role in the pathway toward either cross-coupling or cross-metathesis. The presence of an alkoxy group on the phenyl ring of the olefin entirely determined the synthetic outcome of the reaction, which mirrored the efficiency of the intramolecular electron transfer.
- Okada, Yohei,Chiba, Kazuhiro
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experimental part
p. 1037 - 1042
(2011/04/15)
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- Electrophilic behavior of lithiated 1-alkoxyalkyl and 1-alkylthioalkyl sulfones. Regioselective synthesis of enol ethers and vinyl sulfides
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The readily available 1-alkoxyalkyl and 1-alkylthioalkyl sulfones display electrophilic behavior when lithiated.For example, both react regioselectively with lithiated alkyl sulfones to give enol ethers and vinyl sulfides, respectively.A series of methyl and tert-butyl enol ethers and vinyl sulfides have been prepared. - Keywords: sulfones / alkoxyalkyl sulfones / carbenoids / enol ethers / heterosubstituted carbanions / alkylthioalkyl sulfones / vinyl sulfides
- Habermann, Anne-Kathrin,Julia, Marc,Verpeaux, Jean-Noel,Zhang, Da
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p. 965 - 972
(2007/10/02)
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- ELONGATION OF CARBONYL COMPOUNDS BY UTILIZING ELECTROREDUCTION AS A KEY STEP
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This transformation of aldehydes, ketones and esters to the next higher homologous aldehydes was accomplished by utilizing electroreductive 1,2-elimination as a key step.
- Shono, Tatsuya,Matsumura, Yoshihiro,Kashimura, Shigenori
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p. 1545 - 1548
(2007/10/02)
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