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Updated: Jan 21, 2026
Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
Published on: April 22, 2016
Controlled Radical Homopolymerization of Representative Cationically Polymerizable Vinyl Ethers
Shinji Sugihara1, Ayano Yoshida1, Taka-Aki Kono1
1Department of Applied Chemistry and Biotechnology, Graduate School of Engineering , University of Fukui , 3-9-1 Bunkyo , Fukui 910-8507 , Japan.
Abstract:
Facile direct radical homopolymerization of vinyl ethers without a hydroxy group was achieved up to near full conversion. This polymerization was conducted in water suspension in the presence of lithium hydroxide using a thermally triggered azo-initiator of dimethyl 2,2'-azobis(2-methylpropionate). In the polymerization system, appropriate hydrogen bonding and cation-π interactions under basic conditions are keys to the successful direct radical homopolymerization. The hydrogen bonding between water and vinyl ether oxygen reduces the reactivity of the growing radical, thus suppressing unfavorable side reactions such as β-scission. In addition, Li+ interacts with the oxygen and the vinyl group of vinyl ethers. The vinyl ether tends to be "activated" and the polymerization can be facilitated. Based on the results of free radical polymerization of vinyl ethers, controlled polymerization was also accomplished using the appropriate dithiocarbamate RAFT agent in view of the solubilities of the radical leaving group.
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01:24[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
02:13The Representativeness Heuristic
02:29Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
02:28Structure and Nomenclature of Ethers
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent...
02:36Crown Ethers
02:17Physical Properties of Ethers
An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
Ethers can act as hydrogen bond acceptors, making them more water-soluble than hydrocarbons, but since ethers cannot act as hydrogen bond donors, they are much less soluble in water than alcohols. Ethers are considered...