Die Herstellung von Vinylethern im industriellen Maßstab erfolgt meist durch Umsetzung der entsprechenden Alkohole mit Ethin in Gegenwart basischer Katalysatoren (Reppe-Synthese). Poly(vinyl ether)s with a T g as high as 100 °C have been obtained in the living cationic polymerization of vinyl ethers with a bulky tricyclodecane or tricyclodecene unit using HCl/ZnCl 2 in toluene at –30 °C. Die Herstellung von Vinylethern im industriellen Maßstab erfolgt meist durch Umsetzung der entsprechenden Alkohole mit Ethin in Gegenwart basischer Katalysatoren (Reppe-Synthese). Vinyl ethers have been described in excellent overviews with respect to syntheses, structure and reactivity as well as photo initiated polymerization in cationic and radical UV curing systems [1-3]. endobj Vinyl ethers are ahighly relevant moiety for organic synthe-sis, allowing arich follow-up chemistry. stream These metrics are regularly updated to reflect usage leading up to the last few days. Unlimited viewing of the article PDF and any associated supplements and figures. Due to the high reactivity of these species a kinetic control of the reaction should be feasible preferring the attack of the carbonyl … The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.organomet.0c00163. The cloud points were also influenced largely by the molecular weight and concentration of the polymer. /Kids [3 0 R 19 0 R 32 0 R 134 0 R] In der Flüssigphase wird die stark exotherme Reaktion im Allgemeinen in Gegenwart von Alkalimetallhydroxid- oder Alkalimetallalkoxid-Katalysatoren durchgeführt. Please check your email for instructions on resetting your password. Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Herein, we report a new stereoselective synthesis of vinyl, aryl, alkynyl, alkyl and thio-substituted Z -enamides and enol ethers based on the use of vinylbenziodoxolone … 2.2 Synthesis of Vinyl ester resin (VER) Diglycidyl aniline Epoxy Resin (DGA) was synthesized using Aniline and Epichlorohydrin [refe. jerome.waser@epfl.ch. If released to air, a vapor pressure of 49 mm Hg at 25 °C indicates butyl vinyl ether will exist solely as a vapor in the ambient atmosphere. system. Corresponding authors, a [17] Many carbophilic metalscat-alyze this interesting transformation, such as mercury,[18] silver[19] and ruthenium[20] to name butafew,yet often harsh Using 1-Li-2-OTf-o-C2B10H10 as a precursor, o-carboryne undergoes an efficient [2 + 2] cycloaddition with a large variety of vinyl ethers at room temperature to give a series of carborane-fused cyclobutanes in very good to high isolated yields. Vinyl ethers undergo homopolymerization via a cationic mechanism. the Altmetric Attention Score and how the score is calculated. Ethyl vinyl ether is made by reaction of acetylene and ethanol in presence of a base. A series of poly(2‐methoxyethyl vinyl ether)s with narrow molecular weight distributions and with perfectly defined end groups of varying hydrophobicities was successfully synthesized by base‐assisting living cationic polymerization. This article is cited by The end group was shown to greatly affect the temperature‐induced phase separation behavior of aqueous solutions (lower critical solution temperature‐type phase separation) … For permission to reproduce, republish and Deceptively simple as the structure may appear, there is no single general method by which to synthesize the vinyl (enol) ether functionality. /Count 4 Damit Sie alle Funktionen auf Chemie.DE nutzen können, aktivieren Sie bitte JavaScript. You have to login with your ACS ID befor you can login with your Mendeley account. [16] Hydroalkoxylation of Polymerization is typically initiated with Lewis acids such as boron trifluoride. is available on our Permission Requests page. Find more information on the Altmetric Attention Score and how the score is calculated. Lesen Sie alles Wissenswerte über unser Fachportal chemie.de. << that the correct acknowledgement is given with the reproduced material. Um alle Funktionen dieser Seite zu nutzen, aktivieren Sie bitte die Cookies in Ihrem Browser. Die Vinylierung kann sowohl in flüssiger als auch in der Gasphase durchgeführt werden. You’ve supercharged your research process with ACS and Mendeley! Allyl vinyl ethers are typically prepared by either mercury- or acid-catalyzed vinyl ether exchange with allylic alcohols or acid-catalyzed vinylation of allylic alcohols with acetals. Erfahren Sie mehr über das Unternehmen LUMITOS und unser Team. 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. /Type /Pages The stable VBX reagents were synthesized by stereoselective addition of N- or O-nucleophiles on the corresponding alkynyl reagents in the presence of a catalytic amount of cesium carbonate. %PDF-1.5 Get article recommendations from ACS based on references in your Mendeley library. Microsoft Internet Explorer 6.0 unterstützt einige Funktionen auf Chemie.DE nicht. o-Carboryne (1,2-dehydro-o-carborane) is a very useful synthon for the synthesis of a variety of carborane-functionalized molecules. Some are further confirmed by single-crystal X-ray analyses. This review presents the scope and limitations of these methods according to reaction type, specifically via ether modifications, elimination reactions, … >> redistribute this material, requesters must process their own requests via the RightsLink permission * [15] As ascaffold of interest, many protocols for vinyl ether synthesis have been developed. If you have previously obtained access with your personal account, please log in. /Margins [0 0 0 0] A series of poly(2‐methoxyethyl vinyl ether)s with narrow molecular weight distributions and with perfectly defined end groups of varying hydrophobicities was successfully synthesized by base‐assisting living cationic polymerization. So finden sie unter anderem Verwendung als Monomerbausteine in Polymeren und Copolymeren, in Beschichtungen, Klebstoffen, Druckfarben sowie in strahlungshärtenden Lacken. Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, By continuing to browse this site, you agree to its use of cookies as described in our, I have read and accept the Wiley Online Library Terms and Conditions of Use. A series of poly(2‐methoxyethyl vinyl ether)s with narrow molecular weight distributions and with perfectly defined end groups of varying hydrophobicities was successfully synthesized by base‐assisting living cationic polymerization. 1 publications. Information. /Type /Catalog A vinyl ether is a common and versatile building block in organic synthesis as well as polymer chemistry. A stereospecific and stereoselective, copper-promoted coupling of vinyl pinacol boronate esters and alcohols allows the synthesis of enol ethers in very good yields, is compatible with various functional groups, and occurs at room temperature. /UserRestrictions 136 0 R >> /Type /Page 124 The fast living cationic polymerization of vinyl ethers with SnCl 4 combined with EtAlCl 2 in the presence of an ester as an added base was reported. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Use the link below to share a full-text version of this article with your friends and colleagues. /Contents 146 0 R This reaction is compatible with many functional groups and has a very broad substrate scope ranging from alkyl- to aryl- and to silyl-substituted vinyl ethers. They are increasingly used in radiation curing systems because of a lower toxicity profile than the commonly used acrylic monomers. Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. You do not have JavaScript enabled. We envisioned a vinyl ether synthesis accessible by simple starting materials under mild conditions by exploiting the aforementioned aurated carbocationic intermediates instead of alkynes as electrophiles and simple ketones instead of alcohols or 1,3‐ketones as nucleophiles. /Infix <> /ShowGrid false /ShowGuides false /SnapToGrid false endobj /MediaBox [0 0 612 792] Enamides and enol ethers are valuable building blocks in synthetic chemistry, yet their stereoselective synthesis can be challenging. Sie stellen eine wichtige Stoffgruppe mit breitem Einsatzgebiet dar. /OCProperties <> <> <>] /Order [] >> This article is licensed under a Creative Commons Attribution 3.0 Unported The VBX reagents were used in palladium-catalyzed cross-couplings at room temperature to access Z-enamides and enol ethers. Erfahren Sie, wie LUMITOS Sie beim Online-Marketing unterstützt. o-Carboryne (1,2-dehydro-o-carborane) is a very useful synthon for the synthesis of a variety of carborane-functionalized molecules. Unlimited viewing of the article/chapter PDF and any associated supplements and figures. Butyl vinyl ether's production and use in synthesis and copolymerization may result in its release to the environment through various waste streams.

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