P-Vinylbenzyl ether

The 0-, m- and p-vinylbenzyl ethers of l,2 5,6-di-0-isopropylidene-a-D-glucofuranose have been polymerized, followed by deisopropylidenation, to give amphiphilic polymers which behave as a polysoap in aqueous solution. ... 

Two new synthetic methods for the preparation of functional polymers containing 2-oxazoline pendant groups were developed. The first concerns the synthesis of m- and p-vinylbenzyl ethers of 2-(p-hydroxyphenyl)-2-oxazoline, followed by their radical poljnnerization. 2-(p-Hydroxyphenyl)-2-oxazo-line was reacted with a mixture of m- and p-chloromethylstyrene (60% m and 40% p) under phase transfer catalysis conditions at room temperature. The m-and p-vinylbenzyl ethers of 2-(p-hydroxyphenyl)-2-oxazoline obtained were separated by selective crystallization from methanol. Radical polymerization of these ethers was carried out in dioxane at 60 C, giving polymers with pendant 2-oxazoline groups. 

Figure 4 shows the NMR spectrum of the p-vinylbenzyl ether of 2-(p-hydroxy-phenyl)-2-oxazoline, and Figure 5 shows the NMR spectrum of the... 

A vinyl monomer that acts as an antioxidant is 4-anilino-N-(4-vinylbenzyl)aniline, which can be prepared from p-aminodiphenyl-amine and p-chloromethylstyrene. Similarly, the reaction product of p-hydroxydiphenylamine and p-chloromethylstyrene, which is 4-anilinophenyl-4-vinylbenzyl ether is useful in this way (72). The synthesis is shown in Figure 6.11. 

Certain P-chiral phosphorodiamidite ligands (e.g., 30A, 30B) complex with iridium(I) to form catalysts for promoting reaction of cinnamyl methyl carbonate with ArOH to form chiral aryl a-vinylbenzyl ethers. ... 

The catalytic polyaddition reaction of divinylbenzene and disecondary amines in the presence of a lithium amide yields polyamines with a p-vinylbenzyl (VB) substituent as in equation (21) using iV,iV -diethylethylenediamine. Macromonomers of poly(crown ethers) were also prepared by this method. Macromonomers of polypeptides were synthesized by the ring-opening polymerization of y-benzyl-L-glutamate-N-carboxyanhydride initiated by N-methyl-N-(4-vinylphenethyl) ethylenediamine, and of DL-phenylalanine-N-carboxyanhydride initiated by m, p-vinylbenzyl-... 

Bria et al. synthesized a tetracationic cyclophane-aromatic crown ether-type side-chain poly[2]catenane 59 by employing click chemistry, via route iii (Scheme 17.18) [111]. First, the template-directed coupling reaction between bis(bipyridinium) salt 28 and the alkyne-substituted p-xylylene dibromide 55, in the presence of dinaphtho crown ether 54, afforded an alkyne-functionalized [2]catenane 56 [112], Substitution of the chloro group on styrene-vinylbenzyl chloride copolymer 57 (M = 3.7 kDa, M , = 6.3 kDa) with sodium azide gave the azide-functionalized polymer 58 [83,113-115]. By employing CuS04/ascorbic acid as catalyst [116-120], click chemistry between azide-functionaUzed polymer 58 and alkyne-functionalized [2]catenane 56 afforded the side-chain poly[2]catenane 59, the successful formation of which was confirmed with Fourier transform infrared (FTIR) and NMR analyses. Unfortunately, both of these techniques revealed that the reaction of the azide groups was incomplete, and the observation was ascribed to a Coulombic repulsion of the cyclophane units and steric hindrance caused by the bulky catenane units[121]. 

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