75456-62-1Relevant academic research and scientific papers
One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions
Ezawa, Masatoshi,Togo, Hideo
, p. 2379 - 2384 (2017/05/01)
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.
Palladium-catalyzed reactions of enol ethers: Access to enals, furans, and dihydrofurans
Lauer, Matthew G.,Henderson, William H.,Awad, Amneh,Stambuli, James P.
supporting information, p. 6000 - 6003 (2013/02/25)
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.
Electron transfer-induced four-membered cyclic intermediate formation: Olefin cross-coupling vs. olefin cross-metathesis
Okada, Yohei,Chiba, Kazuhiro
experimental part, p. 1037 - 1042 (2011/04/15)
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.
Electrophilic behavior of lithiated 1-alkoxyalkyl and 1-alkylthioalkyl sulfones. Regioselective synthesis of enol ethers and vinyl sulfides
Habermann, Anne-Kathrin,Julia, Marc,Verpeaux, Jean-Noel,Zhang, Da
, p. 965 - 972 (2007/10/02)
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
ELONGATION OF CARBONYL COMPOUNDS BY UTILIZING ELECTROREDUCTION AS A KEY STEP
Shono, Tatsuya,Matsumura, Yoshihiro,Kashimura, Shigenori
, p. 1545 - 1548 (2007/10/02)
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.
