Vinyl pivalate

Van Der Meer et al. [113] have found that vinyl ester reactivity increases with the electron-withdrawing ability of the ester group. All the measured ester radicals prefer addition of their own monomer to that of ethylene. The observed relative reactivity is mostly affected by polar factors resonance stabilization plays only a minor role. Vinyl ester reactivity grows in the series vinyl iso-butyrate < vinyl butyrate < vinyl propionate < vinyl acetate < vinyl formate vinyl pivalate. 

In an application of the Paal-Knorr pyrrole synthesis, the synthetic equivalents 3 of 1,4-ketoaldehydes were prepared by the radical addition of ketones 4 to vinyl pivalate. Treatment of the intermediates 3 with amines gave pyrroles 5 <03SL75>. Other new extensions of this popular pyrrole synthesis include the preparation of a number of pyrroles from hexane-2,5-dione and amines under solvent-free conditions in the presence of layered zirconium phosphate or phosphonate catalysts <03TL3923>, and the development of a solid-phase variant of this reaction <03SL711>. Likewise, the preparation of iV-acylpyrroles from primary amides and 2,5-dimethoxytetrahydrofuran in the presence of one equivalent of thionyl chloride has also been reported <03S1959>. 

C6H14S dipropyl sulfide 111-47-7 in benzene 1.601 1 11493 C7H1202 vinyl pivalate 3377-92-2 gas 1.844 2... 

Acetates and benzoates of unbranched aldehyde enols react with chloroform in a phase-transfer catalytic system, with benzyltriethylammonium chloride as a catalyst, to form mainly or exclusively products of trichloromethyl anion addition (however, vinyl pivalate under these conditions forms the dichlorocarbene addition product almost exclusively). ... 

In the example below, one enantiomer of compound is acylated by a lipase and the other by a phosphine-catalysed process.10,33 We want the lipase to catalyse the reaction between vinyl pivalate 58 and the R-alcohol, and the phosphine to catalyse the acylation of the S-alcohol using the polymer-bound anhydride 60. But, the lipase must not use the polymer-bound anhydride or the wrong enantiomer of alcohol will end up polymer-bound. Similarly, the phosphine must not react with the vinyl pivalate. Fortunately, the phosphine does not react with the vinyl pivalate and the lipase, which is insoluble, cannot interact with the polymer bound material. Also, the lipase will be kept away from the potentially damaging F-acyIphosphon iurn intermediates. The conditions are described as a Three-Phase System . The three phases are the solution phase and the two separate insoluble phases of the polymer bound anhydride and the cross-linked lipase. 

Materials. VEC was prepared by the catalyzed addition of CO2 to 3,4-epoxy-l-butene using conditions typical of that used industrially [77], then purified by vacuum distillation. Other raw materials were used as received without any additional purification. Mixed xylenes, vinyl acetate (VA), butyl acrylate (BA), butyl methacrylate (BMA), methyl methacrylate (MMA), styrene (St), and t-butyl hydroperoxide were obtained from Aldrich Chemical Company. Lupersol 575 (t-amyl peroxy (2-ethylhexanoate)) was supplied by Elf Atochem. Vazo 67 (2,2 -azobis(2-methylbutyronitrile)) was obtained from DuPont Chemical Company. Vinyl pivalate (NE05), vinyl 2-ethylhexanoate (V2EH), Tergitol NP-40 (non-ionic surfactant) and QP-300 (hydroxy ethyl cellulose) were obtained from Union Carbide Coq)oration. Aerosol OT-75 (surfactant) was obtained from Cytec. Sodium formaldehyde sulfoxylate was obtained from Henkel Corporation. Ethyl 3-ethoxy propionate (EEP), propylene glycol monomethyl ether (PM) and PM acetate (PM Ac) are Eastman Chemical Company products. 

Quite recently. Union Carbide Corp. introduced Vinate monomers. These are vinyl pivalate, vinyl neodecanoate, vinyl neononanoate, vinyl propionate, and vinyl 2-ethylhexanoate. These monomers are said to improve the hydrolytic stability and water resistance of emulsion copolymers [3]. 

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