56679-04-0Relevant articles and documents
Direct evidence for arylmethyl ether coordination of sodium and potassium cations: An electrospray ionization mass spectrometry study
Wang, Keshi,Han, Xianlin,Gross, Richard W.,Gokel, George W.
, p. 7680 - 7686 (1995)
Evidence is presented for complexation between sodium and potassium cation (1 mM) and the simple ethers dibenzyl ether, bis(p-methoxybenzyl) ether, bis(p-nitrobenzyl) ether, or bis(ferrocenylmethyl) ether (concentration 0.01-10 mM). Complexation was asses
Antimony(v) cations for the selective catalytic transformation of aldehydes into symmetric ethers, α,β-unsaturated aldehydes, and 1,3,5-trioxanes
Arias Ugarte, Renzo,Devarajan, Deepa,Mushinski, Ryan M.,Hudnall, Todd W.
supporting information, p. 11150 - 11161 (2016/07/20)
1-Diphenylphosphinonaphthyl-8-triphenylstibonium triflate ([2][OTf]) was prepared in excellent yield by treating 1-lithio-8-diphenylphosphinonaphthalene with dibromotriphenylstiborane followed by halide abstraction with AgOTf. This antimony(v) cation was found to be stable toward oxygen and water, and exhibited exceptional Lewis acidity. The Lewis acidity of [2][OTf] was exploited in the catalytic reductive coupling of a variety of aldehydes into symmetric ethers of type L in good to excellent yields under mild conditions using Et3SiH as the reductant. Additionally, [2][OTf] was found to selectively catalyze the Aldol condensation reaction to afford α-β unsaturated aldehydes (M) when aldehydes with 2 α-hydrogen atoms were used. Finally, [2][OTf] catalyzed the cyclotrimerization of aliphatic and aromatic aldehydes to afford the industrially-useful 1,3,5 trioxanes (N) in good yields, and with great selectivity. This phosphine-stibonium motif represents one of the first catalytic systems of its kind that is able to catalyze these reactions with aldehydes in a controlled, efficient manner. The mechanism of these processes has been explored both experimentally and theoretically. In all cases the Lewis acidic nature of the antimony(v) cation was found to promote these reactions.
N-Alkylation of amines with alcohols over nanosized zeolite beta
Reddy, Marri Mahender,Kumar, Macharla Arun,Swamy, Peraka,Naresh, Mameda,Srujana, Kodumuri,Satyanarayana, Lanka,Venugopal, Akula,Narender, Nama
supporting information, p. 3474 - 3483 (2013/12/04)
Direct N-alkylation of amines with alcohols was successfully performed by using nanosized zeolite beta, which showed the highest catalytic activity among other conventional zeolites. This method has several advantages, such as eco-friendliness, moderate to high yields, and simple work-up procedure. The catalyst was successfully recovered and reused without significant loss of activity and only water is produced as co-product. In addition, imines were also efficiently prepared from the tandem reactions of amines with 2-, 3- and 4-nitrobenzyl alcohols using nanosized zeolite beta.
Photolytic decomposition of dibenzylic sulfites
Grenga, Paolo N.,Stoutenburg, Eric G.,Priefer, Ronny
, p. 4933 - 4937 (2012/11/13)
The photolytic decay of a library of para-substituted dibenzylic sulfites has been evaluated by UV radiation in a Srinivasan-Griffin-Rayonet photochemical reactor in various deuterated solvents. The decay for each dibenzylic sulfite was examined with respect to Swain and Lupton's field constant, F. The rate of photolytic decay varies depending on the identity of the benzyl substituents. Furthermore, it has been observed that the solvent affects both the rate of sulfite photolytic decay as well as final product distribution.
TiCl4-mediated direct N-alkylation of sulfonamides with inactive ethers
Chen, Jiayan,Dang, Ling,Li, Qiang,Ye, Yong,Fu, Shaomin,Zeng, Wei
supporting information; experimental part, p. 595 - 600 (2012/03/27)
A TiCl4-mediated intermolecular or intramolecular direct N-alkylation reaction of sulfonamides with inactive ethers as alkylating agents was successfully achieved. This method provides a novel approach towards N-alkyl sulfonamides from inactive ethers via an easy workup procedure. Georg Thieme Verlag Stuttgart · New York.
Synthesis, DNA binding and antileishmanial activity of low molecular weight bis-arylimidamides
Banerjee, Moloy,Farahat, Abdelbasset A.,Kumar, Arvind,Wenzler, Tanja,Brun, Reto,Munde, Manoj M.,Wilson, W. David,Zhu, Xiaohua,Werbovetz, Karl A.,Boykin, David W.
, p. 449 - 454 (2012/11/07)
The effects of reducing the molecular weight of the antileishmanial compound DB766 on DNA binding affinity, antileishmanial activity and cytotoxicity are reported. The bis-arylimidamides were prepared by the coupling of aryl S-(2-naphthylmethyl)thioimidates with the corresponding amines. Specifically, we have prepared new series of bis-arylimidamides which include 3a, 3b, 6, 9a, 9b, 9c, 13, and 18. Three compounds 9a, 9c, and 18 bind to DNA with similar or moderately lower affinity to that of DB766, the rest of these compounds either show quite weak binding or no binding at all to DNA. Compounds 9a, 9c, and 13 were the most active against Leishmania amazonensis showing IC50 values of less than 1 μM, so they were screened against intracellular Leishmania donovani, showing outstanding activity with IC 50 values of 25-79 nM. Despite exhibiting little in vitro cytotoxicity these three compounds were quite toxic to mice.
High-efficiency conversion of trimethylsilyl ethers to their corresponding ethers using carbon-based solid acid as a new catalyst in heterogeneous mixtures
Shokrollahi, Arash,Zali, Abbas,Pouretedal, Hamid Reza
, p. 371 - 375 (2008/04/01)
Carbon-based solid acid was used as a new catalyst for conversion of trimethylsilyl ethers to their corresponding ethers in heterogeneous mixtures. The experiments were done moderately at room temperature, and high yields in suitable times were obtained under these conditions. Copyright Taylor & Francis Group, LLC.
CaS2O8: An efficient reagent for etherification of alcohols under microwave irradiation in solvent-free conditions
Badri, Rashid,Kiasat, Ali Reza,Nazari, Simin
, p. 589 - 593 (2007/10/03)
A new facile and efficient one-pot method for the synthesis of ethers by the reaction of alcohols with calcium peroxodisulfate under microwave irradiation is described. Copyright Taylor & Francis Group, LLC.
Novel polymer-supported coupling/dehydrating reagents for use in organic synthesis
Fairfull-Smith, Kathryn E.,Jenkins, Ian D.,Longhlin, Wendy A.
, p. 1979 - 1986 (2007/10/03)
Two novel dehydrating reagents 3 and 4, based on a phosphonium anhydride and an oxyphosphonium triflate respectively, were prepared by reaction of the corresponding polymer-supported phosphine oxides with triflic anhydride. Reagent 3, based on the novel phosphorus heterocycle 1,1,3,3-tetraphenyl-2-oxa-1,3- diphospholanium bis(trifluoromethanesulfonate), was found to be a useful reagent for ester and amide formation. A wide range ofcoupling/dehydration-type reactions, such as ester, amide, anhydride, peptide, ether and nitrile formation, were performed in high yield using the more readily prepared polymer-supported triphenylphosphine ditrinate 4, which was easily recovered and re-used several times without loss of efficiency. With primary alcohols, both reagents 3 and 4 provide an alternative to the Mitsunobu reaction, where the use of azodicarboxylates and chromatography to remove the phosphine oxide by-product can be avoided. The use of 4-dimethylaminopyridine allowed the esterification of secondary alcohols with 4 to proceed in high yield but with retention of configuration.
Silica Sulfuric Acid: An Efficient Catalyst for the Direct Conversion of Primary and Secondary Trimethylsilyl Ethers to their Corresponding Ethers under Mild and Heterogeneous Conditions
Zolfigol, Mohammad Ali,Mohammadpoor-Baltork, Iraj,Mirjalili, Bibi Fatemeh,Bamoniri, Abdolhamid
, p. 1877 - 1879 (2007/10/03)
Primary and secondary trimethylsilyl ethers were converted to their corresponding ethers in the presence silica sulfuric acid with good to excellent yields under mild and heterogeneous conditions.
