39834-50-9Relevant academic research and scientific papers
Gold(I)-catalyzed synthesis of unsymmetrical ethers using alcohols as alkylating reagents
Liu, Yongxiang,Wang, Xiaoyu,Wang, Yanshi,Du, Chuan,Shi, Hui,Jin, Shengfei,Jiang, Chongguo,Xiao, Jianyong,Cheng, Maosheng
, p. 1029 - 1036 (2015/03/30)
A microwave-irradiated alcohol-protecting strategy based on gold catalysis utilizing benzyl alcohol, tert-butyl alcohol and triphenylmethanol as alkylating reagents has been developed. This protecting strategy has wide functional group tolerance with satisfactory yields for the majority of the selected alcohols. The mechanism of this transformation was probed with oxygen-18 isotope labelled alcohols assisted by GC-MS techniques and chemical kinetic experiments. This strategy provides an efficient, straightforward and alternative approach to the preparation of benzyl, tert-butyl and trityl ethers in organic synthesis.
Highly efficient protection of alcohols as trityl ethers under solvent-free conditions, and recovery catalyzed by reusable nanoporous MCM-41-SO3H
Gholamzadeh, Zeynab,Naimi-Jamal, Mohammad Reza,Maleki, Ali
, p. 994 - 1001 (2015/01/09)
An efficient method was developed for the protection of alcohols as trityl ethers using triphenylmethanol in the presence of nanoporous MCM-41-SO3H as a heterogeneous catalyst under solvent-free ball-milling at room temperature. Low catalyst loading, high efficiency, reusability are among the advantages of this new solvent-free and environmentally friendly method. The deprotection of the produced trityl ethers was also efficiently achieved using the same catalyst in wet acetonitrile.
Iodine-catalyzed disproportionation of aryl-substituted ethers under solvent-free reaction conditions
Jereb, Marjan,Vrazic, Dejan
, p. 1978 - 1999 (2013/05/22)
Iodine was demonstrated to be an efficient catalyst for disproportionation of aryl-substituted ethers under solvent-free reaction conditions. Variously substituted 1,1,1′,1′-tetraaryldimethyl ethers were transformed into the corresponding diarylketone and diarylmethane derivatives. I 2-catalyzed transformation of 4-methoxyphenyl substituted ethers yielded mono- and dialkylated Friedel-Crafts products as well. Treatment of trityl alkyl and trityl benzyl ethers with a catalytic amount of iodine produced triphenylmethane and the corresponding aldehydes and ketones. The electron-donating substituents facilitated the reaction, while the electron-withdrawing groups retarded it; the difference in reactivity is not very high. Such an observation may be in favour of hydride transfer, predominantly from the less electron rich side of the ether with more stable carbocation formation. With the isotopic studies it was established that a substantial portion of the C-H bond scission took place in the rate-determining step, while the carbonyl oxygen atom originated from the starting ether, and not from the air. The transformation took place under air and under argon, and HI was not a functioning catalyst.
FeCl3-catalyzed tritylation of alcohols in ionic liquids
Sreedhar,Radhika,Neelima,Chowdary,Rao, M. V. Basaveswara
experimental part, p. 3785 - 3795 (2009/12/08)
A simple and efficient protection of alcohols as trityl ethers is described using trityl chloride in the presence of 5mol% FeCl3 as catalyst in ionic liquids at room temperature in shorter reaction times. This mild and efficient method gives access to the
Tris(pentafluorophenyl)borane: a mild and efficient catalyst for the chemoselective tritylation of alcohols
Reddy, Ch. Raji,Rajesh,Balaji,Chethan
, p. 970 - 973 (2008/09/17)
An efficient acid-catalyzed protection of alcohols as trityl ethers is described using triphenylmethanol in the presence of tris(pentafluorophenyl)borane (3 mol %) in dichloromethane at room temperature. The chemoselectivity of this protocol is demonstrat
Convenient method for the preparation of trityl ethers from secondary alcohols
Colin-Messager, Sandrine,Girard, Jean-Pierre,Rossi, Jean-Claude
, p. 2689 - 2692 (2007/10/02)
The preparation of trityl ethers from secondary alcohols (10 mmol) with triphenylmethyl chloride (1.2 eq.) is carried out at room temperature by using DBU (1.4 eq.) as base in CH2Cl2. The high yielding procedure is very simple and it
