56759-09-2Relevant articles and documents
Studies on the Conversions of Diols and Cyclic Ethers. Dehydration of Alcohols and Diols on the Action of Dimethylsulfoxide
Molnar, Arpad,Bartok, Mihaly
, p. 389 - 398 (1981)
The transformations of 13 alcohols and 13 diols in the presence of a small amount dimethylsulfoxide (1/16 mol) were studied.Relationships were found between the type of the hydroxy compound and the selectivity of the transformation, and conclusions were drawn regarding the transformation mechanism.The ether formation observed with certain alcohols proceeds via a carbenium cation.The reaction conditions applied were found suitable for including water elimination from the ditertiary 1,2- and 1,3-diols (pinacol rearrangement, 1,2-elimination).From the 1,4- and 1,5-diols the corresponding oxacycloalkanes can be obtained in good yield.Cyclodehydration occurs by intramolecular nucleophilic substitution, via a concerted mechanism.The effect of DMSO is excerted directly, and proton-catalysis occurs simultaneously.
Method for synthesizing ether by catalyzing alcohol through trimethyl halosilane
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Paragraph 0063-0066, (2020/12/29)
The invention discloses a method for synthesizing ether by catalyzing alcohol through trimethyl halosilane. According to the method, under the conditions of air or nitrogen atmosphere, no solvent andno transition metal catalyst, an alcohol compound is directly used as a raw material, trimethyl halosilane is used as a catalyst, and symmetric or asymmetric ether is synthesized through one-step selective dehydration reaction. According to the method, the use of strong acid, strong base and organic primary halides with high toxicity, instability and higher price is avoided, the synthesis steps are shortened, the synthesis efficiency is improved, the reaction has good selectivity, and a target ether product can be obtained preferentially.
Gold(I)/Chiral N,N′-Dioxide–Nickel(II) Relay Catalysis for Asymmetric Tandem Intermolecular Hydroalkoxylation/Claisen Rearrangement
Li, Jun,Lin, Lili,Hu, Bowen,Zhou, Pengfei,Huang, Tianyu,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 885 - 888 (2017/01/13)
A highly efficient asymmetric cascade reaction between alkynyl esters and allylic alcohols has been realized. Key to success was the combination of a hydroalkoxylation reaction catalyzed by a π-acidic gold(I) complex with a Claisen rearrangement catalyzed by a chiral Lewis acidic N,N′-dioxide–nickel(II) complex. A range of acyclic α-allyl β-keto esters were synthesized in high yields (up to 99 %) with good diastereoselectivities (up to 97:3) and excellent enantioselectivities (up to 99 % ee) under mild reaction conditions. These products can be easily transformed into optically active β-hydroxy esters, β-hydroxy acids, or 1,3-diols.
Organohalide-catalyzed dehydrative O-alkylation between alcohols: A facile etherification method for aliphatic ether synthesis
Xu, Qing,Xie, Huamei,Chen, Pingliang,Yu, Lei,Chen, Jianhui,Hu, Xingen
supporting information, p. 2774 - 2779 (2015/05/27)
Organohalides are found to be effective catalysts for dehydrative O-alkylation reactions between alcohols, providing selective, practical, green, and easily scalable homo- and cross-etherification methods for the preparation of useful symmetrical and unsymmetrical aliphatic ethers from the readily available alcohols. Mechanistic studies revealed that organohalides are regenerated as reactive intermediates and recycled to catalyze the reactions.
Moisture-Tolerant Frustrated Lewis Pair Catalyst for Hydrogenation of Aldehydes and Ketones
Gy?m?re, ádám,Bakos, Mária,F?ldes, Tamás,Pápai, Imre,Domján, Attila,Soós, Tibor
, p. 5366 - 5372 (2015/09/15)
In this paper, we report on the development of a bench-stable borane for frustrated Lewis pair catalyzed reduction of aldehydes, ketones, and enones. The deliberate fine-tuning of structural and electronic parameters of Lewis acid component and the choice of Lewis base provided for the first time, a moisture-tolerant FLP catalyst. Related NMR and DFT studies underpinned the unique behavior of this FLP catalyst and gave insight into the catalytic activity of the resulting FLP catalyst.
Unusual behaviour of dimethyl sulfoxide towards different alcohols in the presence of cyanuric chloride
Chaudhuri, Subrata Kumar,Pramanik, Amit,Roy, Rimi,Khan, Sagar,Ghatak, Avishek,Bhar, Sanjay
, p. 1773 - 1780 (2014/01/17)
Dimethyl sulfoxide in combination with cyanuric chloride in dichloromethane solvent behaved differently with alcohols having different structural features. The products were obtained as methylene acetal or methyl thioether or methyl enethioether depending on the substitution pattern of the alcohols. A plausible mechanism has been proposed on the basis of isotope labeling studies.
Hydrophobic N,N-diarylammonium pyrosulfates as dehydrative condensation catalysts under aqueous conditions
Sakakura, Akira,Koshikari, Yoshiki,Akakura, Matsujiro,Ishihara, Kazuaki
supporting information; experimental part, p. 30 - 33 (2012/02/14)
Oil-soluble N,N-diarylammonium pyrosulfates as nonsurfactant-type catalysts for the dehydrative ester condensation under aqueous conditions are described. Preheat treatment of dibasic sulfuric acid with bulky N,N-diarylamines generates water-tolerant salts of pyrosulfuric acid as active catalyst species. The present catalysts in water can also widely be applied to unusual selective esterifications and dehydrative glycosylation.
Pd(OAc)2/dppf as an efficient and highly active catalyst for the allylation of amines, alcohols and carboxylic acids with 1-phenyl-1-propyne
Wagh, Yogesh S.,Sawant, Dinesh N.,Tambade, Pawan J.,Dhake, Kishor P.,Bhanage, Bhalchandra M.
body text, p. 2414 - 2421 (2011/04/26)
Pd(OAc)2/1,1′-bis(diphenylphosphino)ferrocene as an efficient, highly active catalyst for the allylation of amines, alcohols and carboxylic acids with 1-phenyl-1-propyne has been developed. The effect of various reaction parameters, such as ligand, time, solvent, temperature, metal: ligand ratio and catalyst concentration on yields of the product were investigated. The optimized procedure works well under mild operating conditions and permits rapid generation of a library for various allylated products.
Allylation of 1-phenyl-1-propyne with N- and O-pronucleophiles using polymer supported triphenylphosphine palladium complex as a heterogeneous and recyclable catalyst
Wagh, Yogesh S.,Sawant, Dinesh N.,Dhake, Kishor P.,Deshmukh, Krishna M.,Bhanage, Bhalchandra M.
experimental part, p. 5676 - 5679 (2011/11/06)
Simple methodology for the allylation of various N- and O-pronucleophiles with 1-phenyl-1-propyne as an allylating agent, using PS-TPP-Pd (polymer supported triphenylphosphine palladium) as a highly active heterogeneous recyclable catalyst has been developed. The protocol is applicable for a wide variety of hindered and functionalized aromatic amines, alcohols, and carboxylic acids. The catalyst exhibited remarkable catalytic activity for five consecutive recycles.
Synthesis of early-transition-metal carbide and nitride nanoparticles through the urea route and their use as alkylation catalysts
Yao, Weitang,Makowski, Philippe,Giordano, Cristina,Goettmann, Frederic
scheme or table, p. 11999 - 12004 (2010/05/19)
The use of urea as either a carbon or a nitrogen source enabled the synthesis of various early-transition-metal nitride and carbide nanoparticles (TiN, NbN, Mo2N, 2N, NbCxN1-x, Mo2 C and WC). The abil
