VINYL ACETAMIDE

The nonionic monomer can be acrylamide, N,N-dimethylacrylamide, N-vinyl-2-pyrrolidone, N-vinyl acetamide, or dimethylamino ethyl methacrylate. Ionic monomers are AMPS, sodium vinyl sulfonate, and vinylbenzene sulfonate. The terpolymer should have a molecular weight between 200,000 to 1,000,000 Dalton. 

N-vinyl acetamide, or dimethylamino ethyl methacrylate, 2-acrylamido-2-methylpropane sulfonic acid, sodium vinyl sulfonate, and vinylbenzene sulfonate... 

Yu and co-workers also used CAN to catalyze an aza-Diels-Alder reaction <06TL3545>. Aryl imines were reacted with /V-vinyl pyrrol idin-2-one or IV-methyl-lV-vinyl-acetamide in the presence of 10 mol% CAN resulting in the desired 2,4-cw-tetrahydroquinolines in good yields. 

Alkyl enamides, such as N-(1 -tert-bulyl-viriyl)-acelamide 88 and N-(l-adaman-tyl-vinyl)-acetamide 89, can also be hydrogenated in high enantioselectivity (>99% ee) and activity (TON 5000 TOF >625 h ) with Rh-Me-DuPhos [19]. Remarkably, these bulky alkyl enamides are reduced with the opposite sense of induction, a phenomenon also observed when the bisphospholane Di Square P 63 was applied [87 b]. A computational modeling study by Landis and Feldgus suggested that the reduction of a-alkyl and a-arylenamides involves different coordination pathways [93, 158]. 

Polyelectrolytes Polyether block copolymers Polyvinylamides dimethlyaminoethyl methacrylate For example, poly(7V-methyl-TV-vinyl acetamide) CSM (Sloan, 1995a,b) CSM (Sloan, 1995a,b) CSM (Sloan, 1995a,b) ... 

A conversion degree of more than 95 % was achieved by the poly(N-vinyl succin-imide) and poly(N-vinyl acetamide) methods, while by the poly(N-vinyl carbamate) method essentially pure poly(vinylamine) was obtained. 

C6H11CIO 2,3-dimethyl butanoyl chloride 51760-90-8 408.15 35.134 1,2 8122 C6H11NO N-ethyl-N-vinyl acetamide 3195-79-7 474.25 41.416 2... 

The monomer VAm is not available due to the well known tautomerization equilibrium with acetaldehyde imine. Therefore, polymer-analogous reactions must be employed to synthesize PVAm from suitable precursor polymers, e.g. poly(acrylamide) [53, 54], poly(vinyl acetamide) [55], poly(vinyl carbamate) [56], or poly(vinyl imides) [57]. Some of these polymer-analogous reactions require rather rigorous reaction conditions and side-products and degraded polymer chains disturb the properties of the final product. 

Bauer D, Killmann E, Jaeger W. Flocculation and stabilization of colloidal silica by the adsorption of poly-diallyl-dimethyl-ammoniumchloride (PDAD-MAC) and of copolymers of DADMAC with JV-methyl-lV-vinyl-acetamide (NMVA). Colloid Polym Sci 1998 276 698-708. 

Amino-substituted naphthalenes can be obtained by reacting phenyl vinyl acetamides with triflic anhydride in the presence of a base via the ketene-iminium intermediate (100). ... 

Abstract Recent density functional theory computations of cobalt-catalyzed hydroformylation of propene, A -vinyl acetamide, 1,3-butadiene, acetylene, propyne, and allene and the urea formation from methyl amine as well as Pauson-Khand reaction have been reviewed. The detailed catalytic mechanism and regioselectivity have been discussed and compared with the available experimental data. It shows that modem computational chemistry provides not only qualitative but also quantitative aspects of catalytic reactions. 

In 2004, a comprehensive experimental and theoretical study on the hydroformylation and hydromethoxycarbonylation of A -vinyl acetamide was reported by Klaus et al. [58]. The goal of this study is to get insight into the observed regioselectivity in favor of the branched iso) product (Fig. 5). Both hydroformylation and hydroalkoxycarbonylation have the same reaction mechanism, and they differ only in the step of oxidative addition with hydrogen (H2) leading to aldehydes or alcohol (ROH) yielding amino acid esters. 

Poly(2-vinyl pyridine) Poly(N-vinyl acetamide) SBR... 

KIS Kishida, A., Nakano, S., Kikunaga, Y., and Akashi, M., Synthesis and functionalities of poly(Y-vinylalkylamide). Vll. A novel aqueous two-phase system based on poly(A-vinyl acetamide) and dextran, J. Appl. Polym. Sci., 67, 255, 1998. 

Adhesives for vinyls iV-Propyl-N-vinyl acetamide Britain 1,031,444 1966 Monsanto... 

Vanadium trichloride, 289, 294 VINAC resins see EM A resins, 431 Vinyl abietate, MA copolymerization, 276 A -Vinyl acetamide, MA copolymerization, 660 Vinyl acetate... 

Apparently there is no tendency to form an N-vinyl acetamide in this instance. 

Scheme 5.4 Functionalization of iV-(l-(5-chloropyridin-2-yl)vinyl)acetamide 57. Reprinted (adapted) with permission from Chem. Eur. J. 2009, 15, 5950. Copyright 2009 Wiley-VCH Verlag GmbH Co. KGa. Weinheim...

Scheme 6.4 Competition experiment between butyl vinyl ether and Af-vinyl acetamide. Reprinted (adapted) with permission from J. Am. Chem. Soc. 2012, 134, 443. Copyright 2011 American Chemical Society...

Efficient synthesis of chiral amines is very important to the pharmaceutical industry and there are several different approaches using asymmetric hydrogenation that can be employed, some of which have been discussed in previous sections. For example, ot-methyl benzylamine derivatives, common to many pharmaceuticals, can be synthesised in excellent yields and enantioselectivities from the corresponding vinyl acetamide usually employing rhodium catalysis. 

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