Condensation of perfluoroisobutylene with perfluorinated vinyl alkyl ethers

Conclusions Condensation of perfluoroisobutylene with perfluorovinyl alkyl ethers with CsF catalysis takes place according to a scheme of concerted nueleophilic addition, with participation of the perfluoro-tert-butyl anion as nucleophile and perfluoroisobutylene as electrophile. In the presence of CO₂ the product of concerted perfluoroalkylcarboxylation forms.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1310–1312, June, 1986.     

Reaction of aromatic amines with vinyl alkyl ethers

Summary Aromatic amines such as aniline, p-anisidine, and p-bromoaniline in the presence of BF₃ etherate react with vinyl alkyl ethers to form 1-alkoxy-tetrahydroquinaldine derivatives.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12 p. 2221–2222, December, 1964     

Dipole moments of some alkyl vinyl and alkyl propenyl ethers

Dipole moments of several alkyl vinyl and alkyl propenyl ethers have been determined by the Halverstadt-Kumler method in benzene solution at 293 K. The μ values depend on the bulkiness of the alkyl group present. In the alkyl vinyl ether series, a part of the varying μ values may be ascribed to changes in molecular geometry with varying bulkiness of the alkyl group. Other factors are clearly involved, since even in the alkyl (Z)-propenyl ether series μ values depend significantly on the alkyl group, although the geometry of the molecules remains essentially constant throughout the series. In the latter series, the total dipole moment is linearly related to the Taft's σ^*-values of the alkyl groups:μ/D=?(1.17±0.15)σ^*+(1.29±0.03). This suggests that the variation of μ with the alkyl radical follows from the changing polar character of the alkyl groups, which leads to changes in the value of the group moment μro.     

A regiospecific benzoylation of alkyl vinyl ethers catalysed by palladium

A series of (E)-3-alkoxy-1-arylpropene-1-ones has been prepared by a regiospecific palladium-catalysed aroylation of alkylvinyl ethers.     

Copolymers of butyl acrylate with vinyl alkyl ethers as thickening additives to oils

The possibility of preparing copolymers of butyl acrylate with vinyl butyl and vinyl isobutyl ethers with various ratios of monomeric units by radical polymerization was examined.     

Esters of alternating copolymers of maleic or 2,3-dimethylmaleic anhydride with alkyl vinyl ethers

Maleic anhydride or 2,3-dimethylmaleic anhydride was copolymerized with a number of alkyl vinyl ethers, with AIBN as the initiator. The comonomers were always alternating and were obtained in yields ranging from 15 to 99%. The acid anhydride group in both series of copolymers was converted to the corresponding methyl esters in a two-step reaction. The structure of these polymers was established by elemental analysis and by infrared, ¹H-and ¹³C-NMR spectroscopy. Addtional characterization of these copolymers were carried out by viscosity measurements, differential scanning calorimetry for the determination of glass transition temperatures, and thermal degradation for the determination of the thermal stability of the copolymers.     

Cationic polymerization of vinyl ethers with alkyl or ionic side groups in ionic liquids

Controlled cationic polymerization of isobutyl vinyl ether was demonstrated to proceed in an ionic liquid (IL), 1‐butyl‐3‐octylimidazolium bis(trifluoromethanesulfonyl)imide, using a 1‐(isobutoxy)ethyl acetate/TiCl₄ initiating system, ethyl acetate as an added base, and 2,6‐di‐tert‐butylpyridine as a proton trap reagent. Judicious choices of metal halide catalysts, counteranions of ILs, and additives were essential for controlling the polymerization. The polymerization proceeded much faster in the IL than in CH₂Cl₂, indicating an increased population of ionic active species in the IL due to the high polarity. Polymers with a relatively narrow molecular weight distribution were obtained in the IL with a bis(trifluoromethanesulfonyl)imide ( ) anion even in the absence of an added base, which suggested possible interactions of the counteranion of the IL with the growing carbocations. Moreover, the direct cationic polymerization of a vinyl ether with pendant imidazolium salts, 1‐(2‐vinyloxyethyl)‐3‐methylimidazolium bis(trifluoromethanesulfonyl)imide, proceeded in a homogeneous state in 1‐methyl‐3‐octylimidazolium bis(trifluoromethanesulfonyl)imide. The solubilities of the obtained polymers were readily tuned by counteranion exchange. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016 , 54, 1774–1784     

Structure of the copolymers of alkyl methacrylate and vinyl alkyl ethers,novel viscosity modifiers of lubricating oils

Russian Journal of Applied Chemistry - Copolymers of vinyl butyl ethers and alkyl methacrylates may find use as resource-saving viscosity modifiers of oils that is due to a new approach to their...     

On the interpretation of the 13C NMR spectra of alkyl vinyl and alkyl propenyl ethers

The ¹³C chemical shifts of the E and Z forms of some alkyl propenyl ethers ROCH=CHMe (R = Me, Et, i-Pr, t-Bu) have been measured. The chemical shift of the α carbon of the olefinic system is equally dependent on the alkyl group in both isomers, whereas the shift of the β carbon of the Z isomer is essentially less sensitive to the bulkiness of R than that of the E isomer. The results achieved show that the relatively large variation with R in the chemical shifts of the olefinic carbons in alkyl vinyl ethers (ROCHCH₂ should not be ascribed to a changing p-π conjugation, as has been done in some reports in the literature, but preferably to a changing through-space shielding effect of R on the olefinic carbons. Only a small decrease in the conjugation occurs on going from R = Me to R= t-Bu, which results from a slightly nonplanar structure of the C-O-C=C system in the latter case.     

F and C spectra of fluorinated and partially fluorinated vinyl alkyl ethers

Fluorine, hydrogen, and ¹³C NMR spectral data have been obtained for vinyl alkyl ethers containing fluorines. Some of the molecules are perfluorinated and others include hydrogen, bromine, and chlorine substituents. New generalizations regarding FF spin-spin coupling are developed and used, along with previously recognized correlations, in the confirmation of structures and the assignments of resonances. ¹³C spectroscopy, especially the analysis of ¹³C¹⁹F coupling, is critical in several of the structure determinations. Chlorine isotope effects on fluorine chemical shifts are observed when the chlorine and fluorine are attached to the same carbon, and are also used in the structure analyses. Long-range couplings between fluorines in the vinyl group and fluorines in the alkyl group are interpreted in terms of molecular geometry which allows certain of the alkyl fluorines to “touch” the fluorines cis and gem to the ether oxygen but not the fluorine trans to the oxygen. Two bond ¹³C¹⁹F coupling across the vinyl double bond is found to vary dramatically with the electronegativity of the vinyl substituents in the ethers, in accordance with previous observations for olefins.     

Reaction of arenesulfonyl azides with alkyl vinyl ethers in the presence of ketones. 5-Alkoxy-3-arylsulfonyloxazolidines

2-Methoxy- and 2-ethoxy-1-arylsulfonylaziridines, which are formed by reaction of arenesulfrayl azides with methyl and ethyl vinyl ethers, react with ketones to give 5-alkoxy-2,2-dialkyl-3-arylsulfonyloxazolidines, along with products of dimerization and polymerization of the alkoxyaziridines.Communication V from the series Reaction of Organic Azides with Unsaturated Compounds; see [1] for communication IV. The results of this study are protected by an author's certificate [2].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1613–1618, December, 1976.     

Polymerization of alkyl vinyl ethers in presence of the sulfuric acid — aluminum sulfate complex

Conclusions In presence of the sulfuric acid — aluminum sulfate complex at 20° stereoregular polymers were prepared from ethyl vinyl, propyl vinyl, isopropyl vinyl, and isobutyl vinyl ethers in yields of 80–90%.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 667–670, March, 1967.