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Abstract:

Photoisomerization presents the only direct method for contra-thermodynamic E-Z isomerization of olefins. Synthetic applications of this method have been limited by its reversible nature, which leads to a photostationary-state mixture of both isomers. For the first time, a highly efficient one-pot preparation-isolation of solid ionic liquid Z-cinnamic acids by photoisomerization in acetonitrile solution of ionic liquid E-cinnamic acids is described. © 2010 American Chemical Society.

Registro:

Documento: Artículo
Título:Photoisomerization of ionic liquid ammonium cinnamates: One-pot synthesis-isolation of Z-cinnamic acids
Autor:Salum, M.L.; Robles, C.J.; Erra-Balsells, R.
Filiación:CIHIDECAR-Departamento de Química Orgánica, FCEN, Universidad de Buenos Aires, Pabellón II, 3er P, 1428 - Buenos Aires, Argentina
Año:2010
Volumen:12
Número:21
Página de inicio:4808
Página de fin:4811
DOI: http://dx.doi.org/10.1021/ol1019508
Título revista:Organic Letters
Título revista abreviado:Org. Lett.
ISSN:15237060
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15237060_v12_n21_p4808_Salum

Referencias:

  • Wassescheid, P., Keim, W., (2000) Angew. Chem., Int. Ed. Engl., 39, p. 3772
  • Armstrong, D.W., Zhang, L.-K., He, L., Gross, M.L., (2001) Anal. Chem., 73, p. 3679
  • Crank, J.A., Armstrong, D.W., (2009) J. Am. Soc. Mass Secptrom., 20, p. 1790
  • For selected examples of biosynthesis and plant physiology, studies of trans - and cis -cinnamic acids; Caccamese, S., Azzolina, R., (1979) Chromatographia, 12, p. 545
  • Wong, W.S., Guo, D., Wang, X.L., Yin, Z.Q., Xia, B., Li, N., (2005) Plant Physiol. Biochem., 43, p. 929. , references therein
  • Sun, F.-M., Smith, J.L., Vittimberga, B.M., Traxler, R.W., (2002) ACS Symp. Ser., 816, p. 228
  • For selected reviews on cis - trans photoisomerization and its applications; Mori, T., Inoue, Y., Griesbeck, A.G., Mattay, J., (2005) C=C Photoinduced Isomerization Reactions, p. 417. , In;, Eds.; Synthetic Organic Photochemistry; Marcel Dekker: New York,; p
  • Arai, T., Ramamurthy, V., Schanze, K.S., (1999) Photochemical Cis-trans Isomerization in the Triplet State, p. 131. , In;, Eds.; Organic Molecular Photochemistry, in the Series, Molecular and Supramolecular Photochemistry,; Vol 3, p
  • Rao, V.J., Ramamurthy, V., Schanze, K.S., (1999) Photochemical Cis-trans Isomerization from the Singlet State, p. 169. , In,;, Eds.: Organic Molecular Photochemistry, in the Series, Molecular and Supramolecular Photochemistry,; Vol 3
  • Braun, A.M., Maurette, M.T., Oliveros, E., (1991) Photochemical Technology, p. 500. , Wiley-Chichester,; p
  • Nieuwendaal, R.C., Bertmer, M., Hayes, S.E., (2008) J. Phys. Chem. B, 112, p. 12920
  • Feringa, B.L., Van Delden, R.A., Koumura, N., Geertsema, E.M., (2000) Chem. Rev., 100, p. 1789
  • Klessinger, M., Michl, J., (1995) Excited States and Photochemistry of Organic Molecules, p. 362. , VCH Publishers, Inc.: New York,; p
  • Turro, N.J., Ramamurthy, V., Scaiano, J.C., (2009) Principles of Molecular Photochemistry: An Introduction, p. 319. , University Science Books: Sausalito,; p
  • Lewis, F.D., Yang, J.-S., (1996) J. Phys. Chem., 100, p. 14560. , references therein
  • Raj Gopal, V., Mahipal, A., Reddy, V., Rao, J., (1995) J. Org. Chem., 60, p. 7966

Citas:

---------- APA ----------
Salum, M.L., Robles, C.J. & Erra-Balsells, R. (2010) . Photoisomerization of ionic liquid ammonium cinnamates: One-pot synthesis-isolation of Z-cinnamic acids. Organic Letters, 12(21), 4808-4811.
http://dx.doi.org/10.1021/ol1019508
---------- CHICAGO ----------
Salum, M.L., Robles, C.J., Erra-Balsells, R. "Photoisomerization of ionic liquid ammonium cinnamates: One-pot synthesis-isolation of Z-cinnamic acids" . Organic Letters 12, no. 21 (2010) : 4808-4811.
http://dx.doi.org/10.1021/ol1019508
---------- MLA ----------
Salum, M.L., Robles, C.J., Erra-Balsells, R. "Photoisomerization of ionic liquid ammonium cinnamates: One-pot synthesis-isolation of Z-cinnamic acids" . Organic Letters, vol. 12, no. 21, 2010, pp. 4808-4811.
http://dx.doi.org/10.1021/ol1019508
---------- VANCOUVER ----------
Salum, M.L., Robles, C.J., Erra-Balsells, R. Photoisomerization of ionic liquid ammonium cinnamates: One-pot synthesis-isolation of Z-cinnamic acids. Org. Lett. 2010;12(21):4808-4811.
http://dx.doi.org/10.1021/ol1019508