Phenyl Vinyl Sulfoxide Research Articles

Synthesis and electrical properties of polyacetylene copolymers from poly(phenyl vinyl sulfoxide) and its oxidized products

Poly(phenyl vinyl sulfoxide), a soluble precursor to polyacetylene, was synthesized by anionic polymerization. Different fractions of the thermally labile phenylvinyl sulfoxide pendant groups were oxidized to themally stable phenyl vinyl sulfones in order to control the degree of conjugation in the polymer main chain after elimination. The mean conjugation length (MCL), the total number percentage of nonconjugated structures or nonconductive defects, and the weight end volume fractions of acetylene units in the eliminted copolymers were calculated and correlated with their bulk conductivities after doping with iodine. A sigmoidal dependence on conductivity and a minimum in the dissipation factor measurement wre observed for the four calculated variables over the full composition range

Separability of SO2 from SO2/N2 mixture through sulfoxide‐modified poly(vinyl alcohol) and cellulose membranes

AbstractSeparability of SO2 from mixtures of SO2 and N2 gases was studied for membranes of poly(vinyl alcohol) (PVA) and cellulose modified with methyl, ethyl, t‐butyl, and phenyl vinyl sulfoxides. Of these sulfoxide‐modified polymers, the phenyl vinyl sulfoxide‐modified PVA membranes were found to give the best separation of SO2. In the phenyl vinyl sulfoxide modified PVA membranes, the permeability coefficient of SO2 increased with sulfoxide content while separability of SO2 was maximum at a sulfoxide content of 23.5 mol %; the separation factor of SO2 was about 170 at this sulfoxide content. © 1993 John Wiley & Sons, Inc.

Hydroformylation of vinyl sulfones and sulfoxides catalyzed by a zwitterionic rhodium complex. A diastereoselective process

The hydroformylation of unsaturated sulfones and sulfoxides catalyzed by η 6 -C 6 H 5 B-Ph 3 Rh + (1,5-COD) (1) was achieved in excellent yield and regiocontrol, with exclusive formation of branched-chain aldehydes. In the case of phenyl vinyl sulfoxide, evidence is presented for stereoselectivity in the reaction

Electrophilic ene-type reactions of phenyl vinyl sulfoxide with alkenes

Phenyl vinyl sulfoxide 1 can be made to react as an α,β-dicarbocation with alkenes by formation of one, or two new C–C bonds. These reactions take place at or below room temperature, under the conditions of the Pummerer reaction, i.e. trifluoroacetic acid and its anhydride. The key step is an electrophilic ene-type reaction between a thionium ion and the alkene. The primary β-trifluoroacetoxy sulfides thus formed then undergo rearrangement via an episulfonium ion to the more stable, secondary isomer.

Synthesis of polyacetylene by chemical modification of poly(phenyl vinyl sulfoxide)

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of polyacetylene by chemical modification of poly(phenyl vinyl sulfoxide)D. Reibel, R. Nuffer, and C. MathisCite this: Macromolecules 1992, 25, 26, 7090–7095Publication Date (Print):December 1, 1992Publication History Published online1 May 2002Published inissue 1 December 1992https://doi.org/10.1021/ma00052a003RIGHTS & PERMISSIONSArticle Views206Altmetric-Citations28LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (729 KB) Get e-Alerts Get e-Alerts

Diels-Alder reactions of 1,5-dihydropyrano[3,4- b]pyrrol-5(1 H)-ones, pyrrole-2,3-quinodimethane analogues; a new synthesis of indoles

The pyrano[3,4- b]pyrrol-5-(1 H)-ones 7 are stable cyclic analogues of pyrrole-2,3-quinodimethane, and undergo Diels-Alder reaction with a range of acetylenes (dimethyl acetylenedicarboxylate, ethyl propiolate, ethyl trimethylsilylpropynoate, benzyne and the acetylene equivalent, phenyl vinyl sulfoxide), to give, after loss of carbon dioxide, indoles. The Diels-Alder reaction can be extended to the intramolecular variant to give cycloalka-[ e]- and [ g]-indoles.

“Ene-type” addition of alkenes to phenyl vinylsulfoxide

Phenyl vinylsulfoxide reacts under acylating conditions (TFA, TFAA) with isobutene to give double “ene” α,β- adduct. Propene and other alkenes examined afford a β-“ene” alkylation accompanied by trifluoroacetoxylation at the same carbon atom.

ChemInform Abstract: Novel Formation of Isomeric Bicyclo(3.2.0)heptan‐1‐ols from Phenyl Vinyl Sulfoxide and the Cyclopentanone Lithium Enolate Generated by Conjugate Addition of Lithiated E‐But‐2‐enyldiphenylphosphine Oxide to 2‐Methylcyclopent‐2‐enone.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A facile total synthesis of isoquinolone alkaloids

Four isoquinolone alkaloids, N-methylcorydaldine, 8a oxyhydrastinine 8b, 6,7-dimethoxy-2-methylisocarbostyril 9a and doryanine 9b, have been efficiently synthesized from phenyl vinyl sulfoxide via the Pummerer type rearrangement as a key step.

Novel formation of isomeric bicyclo[3.2.0]heptan-1-ols from phenyl vinyl sulfoxide and the cyclopentanone lithium enolate generated by conjugate addition of lithiated (E)-but-2-enyldiphenylphosphine oxide to 2-methylcyclopent-2-enone

Novel formation of isomeric bicyclo[3.2.0]heptan-1-ols from phenyl vinyl sulfoxide and the cyclopentanone lithium enolate generated by conjugate addition of lithiated (E)-but-2-enyldiphenylphosphine oxide to 2-methylcyclopent-2-enone

A Rapid Synthesis of Substituted 4-Hydroxymethyl-3-Chromene from 2′-Hydroxyacetophenone and Phenyl Vinyl Sulfoxide

A two-step synthesis of 6-alkyl-4-hydroxymethyl-3-chromene (6-alkyl-4-hydroxymethyl-2H-1-benzopyran) from addition of phenyl vinyl sulfoxide carbanion to 5′-alkyl-2′-hydroxyacetophenone is described. Application to the synthesis of 4-methyl-3-chromene (4-methyl-2H-1-benzopyran) and 4,4-dimethylchroman (3,4-dihydro-4,4-dimethyl-2H-1-benzopyran) is also presented.

ChemInform Abstract: Synthesis of α‐ and β‐Nicotyrines. Use of Phenyl Vinyl Sulfoxide as a Masked Equivalent of Acetylene Dipolarophile.

AbstractThe N‐oxides (III), prepared by coupling the acetylpyridines (I) with the hydroxylamine (II), react with phenyl vinyl sulfoxide (IV), yielding the nicotyrines (VII).

Synthesis of .alpha.- and .beta.-nicotyrines. Use of phenyl vinyl sulfoxide as a masked equivalent of acetylene dipolarophile

Synthesis of .alpha.- and .beta.-nicotyrines. Use of phenyl vinyl sulfoxide as a masked equivalent of acetylene dipolarophile

Microbial Asymmetric Oxidation of 2-Alkoxyethylsulfides and a Facile Synthesis of Chiral Vinyl Sulfoxide

Abstract 2-Alkoxyethyl phenyl sulfides were oxidized by incubation with Rhodococcus equi IFO 3730 to afford chiral sulfoxides of high enantio excess. Phenyl vinyl sulfoxide and 2-hydroxyethyl phenyl sulfoxide were obtained from microbial oxidation products without any loss of their optical purities.

The structures of different diastereomers of bicyclo[2.2.1]hept-5-en-2-yl phenyl sulfoxide.

Three diastereomers of bicyclo[2.2.1]hept-5-en-2-yl phenyl sulfoxide were prepared by Diels-Alder [4 + 2] cycloadditions between phenyl vinyl sulfoxide and cyclopentadiene. The isomers were separated by column chromatography on silica gel and repeated recrystallizations gave the pure racemates of three of the four possible diastereomers. It proved to be impossible to assign the stereochemistry of the products from low-resolution NMR spectra. The X-ray diffraction studies of the three diastereomers showed the relative configuration at the two chiral centers and these stereochemical assignments were, subsequently, correlated with the two-dimensional NMR spectroscopic results. Compound (I), exo-(2R*,8S*)-bicyclo[2.2.1]hept-5-en-2-yl phenyl sulfoxide [or the exo-(2S*,8R*)-isomer], C13H14OS, Mr = 218.31, orthorhombic, P2(1)2(1)2(1), a = 10.517 (2), b = 10.914 (2), c = 9.642 (3) A, V = 1106.7 A3, Z = 4, Dx = 1.31 g cm-3, Cu K alpha, lambda = 1.54178 A, mu = 22.14 cm-1, F(000) = 464, T = 138 (2) K, R = 0.042 for 1151 data. Compound (II), exo-(2RS,8RS)-bicyclo[2.2.1]hept-5-en-2-yl phenyl sulfoxide, C13H14OS, Mr = 218.31, triclinic, P1, a = 8.775 (4), b = 16.353 (8), c = 7.804 (3) A, alpha = 90.67 (3), beta = 101.08 (4), gamma = 85.64 (5) degrees, V = 1095.8 A3, Z = 4, Dx = 1.32 g cm-3, Mo K alpha, lambda = 0.71069 A, mu = 2.18 cm-1, F(000) = 464, T = 138 (2) K, R = 0.062 for 3264 data. The two molecules in the asymmetric unit are crystallographically independent, but their conformations are similar.(ABSTRACT TRUNCATED AT 250 WORDS)

ORGANIC REACTIONS WITHOUT SOLVENT: MICHAEL ADDITIONS ON AN UNSATURATED SULFONE AND SULFOXIDE

Abstract Solid-liquid phase transfer catalysis in the absence of any solvent efficiently promotes Michael additions of nitro alkanes and of diethyl N-acetylaminomalonate to phenyl vinyl sulfone and to phenyl vinyl sulfoxide. The adduct of the Michael addition to diethyl N-acetylaminomalonate to phenyl vinyl sulfoxide was converted by distillation under partial vacuum to diethyl N-acetylamino vinyl malonate which gave (±)-vinylglycine by hydrochloric acid catalysis.

Synthesis of Sulfoxide-Modified Cellulose Derivatives Designed for the Permselective Membrane of Sulfur Dioxide

Abstract The Michael type addition reaction of cellulose with a series of vinyl sulfoxides, namely methyl vinyl sulfoxide, ethyl vinyl sulfoxide, t-butyl vinyl sulfoxide, and phenyl vinyl sulfoxide, was performed with NaOH as a catalyst to produce 2-(alkyl- or arylsulfinyl)ethyl cellulose derivatives. The high permselectivity of sulfur dioxide against nitrogen and oxygen was achieved through these sulfoxide modified cellulose membranes.

Preparation and reactions of polymeric azides. IV. Reaction with phenyl vinyl sulfoxide

Journal of Polymer Science: Polymer Chemistry EditionVolume 22, Issue 9 p. 2293-2294 Note Preparation and reactions of polymeric azides. IV. Reaction with phenyl vinyl sulfoxide Hyman L. Cohen, Hyman L. Cohen Research Laboratories, Eastman Kodak Company, Rochester, New York 14650Search for more papers by this author Hyman L. Cohen, Hyman L. Cohen Research Laboratories, Eastman Kodak Company, Rochester, New York 14650Search for more papers by this author First published: September 1984 https://doi.org/10.1002/pol.1984.170220930Citations: 4AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article.Citing Literature Volume22, Issue9September 1984Pages 2293-2294 RelatedInformation

Synthesis of [1.1.1.1]paracylophane

The title compound 1 has been synthesized by a route involving acyloin cyclization, pyrolytic elimination of a diacetate 5 derived from the acyloin 4 , and the Diels-Alder reaction of the resultant 1,3-diene 6A with phenyl vinyl sulfoxide.

Facile construction of C 10 modified prostaglandin precursors. diyl trapping reactions using phenyl vinyl sulfoxide and phenyl vinyl sulfone.

The application of 1,3-diyl trapping reactions to the synthesis of commonly used prostanoid precursors is described.