Preferences help
enabled [disable] Abstract
Number of results
2017 | 14 | 173–186
Article title

Substytucja octanów allilowych nukleofilami fosforowymi oraz zawierającymi atom fosforu

Title variants
Languages of publication
Celem projektu było zbadanie reaktywności wybranych octanów allilowych w substytucji nukleofilami fosforowymi lub karboanionami zawierającymi atom fosforu. W reakcji zastosowano fosforyn trietylowy, fosfonooctan trietylowy oraz metyleno- bisfosfonian tetraetylowy. Produktami były α,β-nienasycone estry zawierające grupę lub grupy fosfonianowe, dla których następnie przeprowadzono hydrolizę do form kwasowych z użyciem bromotrimetylosilanu. W wyniku tego otrzymano szereg związków wielofunkcyjnych, których struktury poddano charakterystyce technikami spektroskopowymi. W przypadku związków polikarboksylowych napotkano trudności z wydzieleniem oczekiwanych produktów.
The purpose of the project was to investigate the reactivity of selected allyl acetates for substitution with phosphorus nucleophiles or phosphorus-containing carboanions. Triethyl phosphite, triethyl phosphonoacetate and tetraethyl methylenedi- phosphonate were used for the reaction. The products are α,β-unsaturated esters containing one or more phosphonate moieties for which hydrolysis to the acidic form was performed using bromotrimethylsilane. As a result, we obtained a variety of multifunctional compounds. Their structures were characterized with spectroscopic methods. For policarboxylic compounds, we encountered issues with purification of the obtained products.
  • Politechnika Wrocławska
  • Basavaiah D., Pandiaraju S., Nucleophilic Addition of Triethyl Phosphite to Acetates of the Baylis-hillman Adducts: Stereoselective Synthesis of (E)- and (Z)-allylphosphonates, “Tetrahedron” 1996, No. 52, s. 2261.
  • Basavaiah D., Reddy B. S., Badsara S. S., Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry, “Chem. Rev.” 2010, No. 110, s. 5447.
  • Basavaiah D., Veeraraghavaiah G., The Baylis-Hillman Reaction: A Novel Concept for Creativity in Chemistry, “Chem. Soc. Rev.” 2012, No. 41, s. 68.
  • Baylis A. B., Hillman M. E. D., German Patent 2155113 [Chem. Abstr. 77, 34174q], 1972.
  • Guindon Y., Bencheqroun M., Bouzide A., Synthesis of Postulated Molecular Probes: Stereoselective Free-Radical-Mediated C-Glycosylation in Tandem with Hydrogen Transfer, “J. Am. Chem. Soc.” 2005, No. 127 (2), s. 554–558.
  • Janecki T., Bodalski R., A Convenient Method for the Synthesis of Substituted 2-Metho- xycarbonyl- and 2-Cyano-allylphosphonates. The Allyl Phosphite – Allylphosphonate Rearrangement, “Synthesis” 1990, s. 799.
  • Krawczyk E., Owsianik K., Skowrońska A., A Regio- and Stereoselective Reactions be- tween Cyclic Baylis-Hillman Type Adducts and N-nucleophiles and P-nucleophiles, “Tetra- hedron” 2005, No. 61, s. 1449.
  • Majewski P., New Synthetic Route to Dialkylphosphinic Acids, “Phosphorus, Sulfur and Silicon” 1989, No. 45, s. 151.
  • McFadden H. G., Harris R. L. N., Jenkins C. L. D, Potential Inhibitors of Phosphoenol- pyruvate Carboxylase. II. Phosphonic Acid Substrate Analogues Derived from Reaction of Trialkyl Phosphites with Halomethacrylates, “Aust. J. Chem.” 1989, No. 42, s. 301.
  • Morita K., Suzuki Z., Hirose H., A Tertiary Phosphine-catalyzed Reaction of Acrylic Compounds with Aldehydes, “Bull. Chem. Soc. Jpn.” 1968, No. 41, s. 2815.
  • Shi M., Wang F.-J., Zhao M.-X., Wei Y., The Chemistry of the Morita-Baylis-Hillman Re- action, RSC Publishing, Cambridge 2011.
  • Takagi R., Miwa Y., Nerio T., Inoue Y., Matsumura S., Ohkata K., Stereochemical Inve- stigation on the Construction of Poly-functionalized Bicyclo[3.3.1]nonenones by Suc- cessive Michael Reactions of 2-cyclohexenones, “Organic & Biomolecular Chemistry” 2007, No. 5 (2), s. 286–300.
  • Talma M., Mucha A., P-C Bond Formation in Reactions of Morita-Baylis-Hillman Ad- ducts with Phosphorus Nucleophiles, “Arkivoc” 2017, s. 324.
  • Wei Y., Shi M., Recent Advances in Organocatalytic Asymmetric Morita-Baylis-Hill- man/aza-Morita-Baylis-Hillman Reactions, “Chem. Rev.” 2013, No. 113, s. 6659.
Document Type
Publication order reference
YADDA identifier
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.