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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 23
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Articles

Novel synthesis routes for the preparation of low toxic vinyl ester and vinyl carbonate monomers

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Pages 3629-3641 | Received 24 Jul 2020, Published online: 22 Sep 2020

References

  • Schuster, M.; Turecek, C.; Kaiser, B.; Stampfl, J.; Liska, R.; Varga, F. Evaluation of Biocompatible Photopolymers I: Photoreactivity and Mechanical Properties of Reactive Diluents. J. Macromol. Sci. A 2007, 44, 547–557. DOI: 10.1080/10601320701235958.
  • Schuster, M.; Turecek, C.; Mateos, A.; Stampfl, J.; Liska, R.; Varga, F. Evaluation of Biocompatible Photopolymers II: further Reactive Diluents. Monatsh. Chem. 2007, 138, 261–268. DOI: 10.1007/s00706-007-0609-2.
  • Fouassier, J.-P. Photoinitiation, Photopolymerization, and Photocuring: Fundamentals and Applications; Hanser: New York, 1995.
  • Nichol, J. W.; Koshy, S. T.; Bae, H.; Hwang, C. M.; Yamanlar, S.; Khademhosseini, A. Cell-Laden Microengineered Gelatin Methacrylate Hydrogels. Biomaterials 2010, 31, 5536–5544. DOI: 10.1016/j.biomaterials.2010.03.064.
  • Heller, C.; Schwentenwein, M.; Russmüller, G.; Koch, T.; Moser, D.; Schopper, C.; Varga, F.; Stampfl, J.; Liska, R. Vinylcarbonates and Vinylcarbamates: Biocompatible Monomers for Radical Photopolymerization. J. Polym. Sci. A Polym. Chem. 2011, 49, 650–661. DOI: 10.1002/pola.24476.
  • Mautner, A.; Steinbauer, B.; Orman, S.; Russmüller, G.; Macfelda, K.; Koch, T.; Stampfl, J.; Liska, R. Tough Photopolymers Based on Vinyl Esters for Biomedical Applications. J. Polym. Sci. A Polym. Chem. 2016, 54, 1987–1997. DOI: 10.1002/pola.28065.
  • Mautner, A.; Qin, X.; Wutzel, H.; Ligon, S. C.; Kapeller, B.; Moser, D.; Russmueller, G.; Stampfl, J.; Liska, R. Thiol‐Ene Photopolymerization for Efficient Curing of Vinyl Esters. J. Polym. Sci. A Polym. Chem. 2013, 51, 203–212. DOI: 10.1002/pola.26365.
  • Husar, B.; Liska, R. Vinyl Carbonates, Vinyl Carbamates, and Related Monomers: Synthesis, Polymerization, and Application. Chem. Soc. Rev. 2012, 41, 2395–2405. DOI: 10.1039/c1cs15232g.
  • Husar, B.; Heller, C.; Schwentenwein, M.; Mautner, A.; Varga, F.; Koch, T.; Stampfl, J.; Liska, R. Biomaterials Based on Low Cytotoxic Vinyl Esters for Bone Replacement Application. J. Polym. Sci. A Polym. Chem. 2011, 49, 4927–4934. DOI: 10.1002/pola.24933.
  • Heller, C.; Schwentenwein, M.; Russmueller, G.; Varga, F.; Stampfl, J.; Liska, R. Vinyl Esters: Low Cytotoxicity Monomers for the Fabrication of Biocompatible 3D Scaffolds by Lithography Based Additive Manufacturing. J. Polym. Sci. A Polym. Chem. 2009, 47, 6941–6954. DOI: 10.1002/pola.23734.
  • Sabel, A.; Smidt, J.; Jira, R.; Prigge, H. Exchange of Vinyl and Other Unsaturated Groups between Esters and Carboxylic Acids Catalyzed by Platinum Metal Salts. Chem. Ber. 1969, 102, 2939–2950. &. DOI: 10.1002/cber.19691020908.
  • Lobell, M.; Schneider, M. P. Synthesis of Hydroxycarboxylic Acid Vinyl Esters. Synthesis 1994, 1994, 375–377. DOI: 10.1055/s-1994-25479.
  • Weinhouse, M. I.; Janda, K. D. A New Methodology for the Preparation of Vinyl Esters. Synthesis 1993, 1993, 81–83. DOI: 10.1055/s-1993-25802.
  • Wang, Z. Einhorn Acylation. In Comprehensive Organic Name Reactions and Reagents; Wang, Z., Ed.; Wiley: New York, 2010; pp. 967–970.
  • Mori, M.; Nakanishi, M.; Kajishima, D.; Sato, Y. A Novel and General Synthetic Pathway to Strychnos Indole Alkaloids: Total Syntheses of (-)-Tubifoline, (-)-Dehydrotubifoline, and (-)-Strychnine Using Palladium-Catalyzed Asymmetric Allylic Substitution. J. Am. Chem. Soc. 2003, 125, 9801–9807. DOI: 10.1021/ja029382u.
  • Pozo, M.; Gotor, V. Chiral Carbamates through an Enzymatic Alkoxycarbonylation Reaction. Tetrahedron 1993, 49, 4321–4326. DOI: 10.1016/S0040-4020(01)85748-3.
  • Kreutzberger, C. B. A.; Olofson, R. A.; Buszek, K. R. Vinyl Chloroformate. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 2001.
  • Kung, F. E. Unsaturated Chlorocarbonates and Method of Preparation; Google Patents, 1945.
  • Malfroot, T.; Piteau, M. Industrial Synthesis of Vinyl Chloroformates; Societe Nationale des Poudres et Explosifs: France, 1979; p. 9.
  • Olofson, R. A.; Cuomo, J. A Useful Route to Alkenyl s-Phenyl Thiocarbonates: Reagents for the Introduction of the Enyloxycarbonyl Moiety in Synthesis. J. Org. Chem. 1980, 45, 2538–2541. DOI: 10.1021/jo01300a066.
  • Rendler, S.; Oestreich, M. Hypervalent Silicon as a Reactive Site in Selective Bond-Forming Processes. Synthesis 2005, 2005, 1727–1747. DOI: 10.1055/s-2005-869949.
  • Lee, I.; Shim, C. S.; Chung, S. Y.; Kim, H. Y.; Lee, H. W. Cross-Interaction Constants as a Measure of the Transition-State Structure. Part 1. The Degree of Bond Formation in Nucleophilic Substitution Reactions. J. Chem. Soc, Perkin Trans. 2 1988, 1988, 1919–1923. DOI: 10.1039/p29880001919.
  • Olofson, R. A.; Dang Vu, A.; Morrison, D. S.; De Cusati, P. F. Simple One-Step Preparations of Vinylic Carbonates from Aldehydes. J. Org. Chem. 1990, 55, 1–3. DOI: 10.1021/jo00288a001.
  • Dehmlow, E. V.; Fastabend, U.; Keßler, M. A One-Pot Synthesis of Trimethylsilyl Fluoride. Synthesis 1988, 1988, 996–997. DOI: 10.1055/s-1988-27783.
  • Sladkov, A. M.; Petrov, G. S. Acylation of the Enol Form of Acetaldehyde. Zh. Obshch. Khim. 1954, 24(3), 450–454.
  • Yakubovich, A. Y.; Razumovskii, V. V.; Vostrukhina, Z. N.; Rozenshtein, S. M. Syntheses of Vinyl Monomers. Zh. Obshch. Khim. 1958, 28(7), 1930–1936.
  • Luo, C. J.; Stride, E.; Edirisinghe, M. Mapping the Influence of Solubility and Dielectric Constant on Electrospinning Polycaprolactone Solutions. Macromolecules 2012, 45, 4669–4680. DOI: 10.1021/ma300656u.
  • Richards, T. W.; Shipley, J. The Dielectric Constants of Typical Aliphatic and Aromatic Hydrocarbons, Cyclohexane, Cyclohexanone, and Cyclohexanol. J. Am. Chem. Soc. 1919, 41, 2002–2012. DOI: 10.1021/ja02233a017.
  • McMurry, J. Organic Chemistry; Brooks/Cole Cengage Learning: Australia, 2012.
  • Kim, J. K.; Caserio, M. C. Acyl Transfer Reactions in the Gas Phase. Ion-Molecule Chemistry of Vinyl Acetate. J. Am. Chem. Soc. 1982, 104, 4624–4629. DOI: 10.1021/ja00381a020.
  • Olofson, R. A.; Cuomo, J. A Regiospecific and Stereospecific Route to Enol Carbonates and Carbamates: Closer Look at a “Naked Anion”. Tetrahedron Lett. 1980, 21, 819–822. DOI: 10.1016/S0040-4039(00)71514-0.
  • Piteau, M. D. A.; Malfroot, T. A. Isopropenyl Chloroformate and Isopropenyl and Vinyl Chlorothioformates; Societe Nationale des Poudres et Explosifs: France, 1978; p. 23.
  • Wren, C. D. A Review of Metal Accumulation and Toxicity in Wild Mammals: I. Environ. Res. 1986, 40, 210–244. DOI: 10.1016/S0013-9351(86)80098-6.
  • Nunez, I. M.; Seelye, D. E. Process for Preparing Vinyl Chloroformate; Bausch & Lomb Incorporated: New York, 2013; p. 33. Chemical Indexing Equivalent to 157:493128 (US).
  • Lin, C.-C.; Anseth, K. S. PEG Hydrogels for the Controlled Release of Biomolecules in Regenerative Medicine. Pharm. Res. 2009, 26, 631–643. DOI: 10.1007/s11095-008-9801-2.
  • Mautner, A.; Steinbauer, B.; Russmüller, G.; Lieber, R.; Koch, T.; Stampfl, J.; Liska, R. Vinyl Carbonate Photopolymers with Improved Mechanical Properties for Biomedical Applications. Des. Monomers Polym. 2016, 19, 437–444. DOI: 10.1080/15685551.2016.1169378.
  • Mautner, A.; Qin, X.; Kapeller, B.; Russmueller, G.; Koch, T.; Stampfl, J.; Liska, R. Efficient Curing of Vinyl Carbonates by Thiol-Ene Polymerization. Macromol. Rapid Commun. 2012, 33, 2046–2052. DOI: 10.1002/marc.201200502.
  • Orman, S.; Hofstetter, C.; Aksu, A.; Reinauer, F.; Liska, R.; Baudis, S. Toughness Enhancers for Bone Scaffold Materials Based on Biocompatible Photopolymers. J. Polym. Sci. A Polym. Chem. 2019, 57, 110–119. DOI: 10.1002/pola.29273.
  • Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities. J. Org. Chem. 1997, 62, 7512–7515. DOI: 10.1021/jo971176v.
  • Ishihara, K.; Nakajima, N. Structural Aspects of Acylated Plant Pigments: Stabilization of Flavonoid Glucosides and Interpretation of Their Functions. J. Mol. Catal. B Enzym. 2003, 23, 411–417. DOI: 10.1016/S1381-1177(03)00106-1.