Artículo
Calandra, J.; Postigo, A.; Russo, D.; Nudelman, N.S.; Tereñas, J.J. "Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: Thermal and photochemical initiation" (2010) Journal of Physical Organic Chemistry. 23(10):944-949
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Abstract:
The classical radical-based hydrosilylation reaction of organic compounds bearing C-C multiple bonds is usually carried out in organic solvents and is herein presented in water with both hydrophobic and hydrophilic substrates. Thermal and photochemical initiations are used to accomplish the radical-induced hydrosilylation reaction of C-C multiple bonds in water with tris(trimethylsilyl)silane ((Me3Si)3SiH). Photochemical radical initiation in the absence of a chemical radical precursor other than the silane is found to be a very efficient and convenient method to induce the hydrosilylation reaction of C-C multiple bonds of organic compounds with (Me3Si)3SiH in water. This new alternate radical-based methodology studied in water is confronted with the classical radical thermal initiation of hydrosilylation reactions triggered through the thermal decomposition of azo compounds. Copyright © 2010 John Wiley and Sons, Ltd.
Registro:
| Documento: | Artículo |
| Título: | Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: Thermal and photochemical initiation |
| Autor: | Calandra, J.; Postigo, A.; Russo, D.; Nudelman, N.S.; Tereñas, J.J. |
| Filiación: | Faculty of Science, University of Belgrano, Villanueva 1324, CP 1426 Buenos Aires, Argentina Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 3er piso, CP1428, Buenos Aires, Argentina |
| Palabras clave: | photochemical initiation; radical reactions in water; silyl radicals; Azo compound; Chemical radicals; Hydrophobic and hydrophilic; Hydrosilylation reaction; Multiple bonds; Photochemical initiation; Radical initiations; Radical reactions; silyl radicals; Thermal decompositions; Thermal initiations; Tris(trimethylsilyl)silane; Chemical compounds; Hydrosilylation; Organic solvents; Pyrolysis; Reaction kinetics; Photochemical reactions |
| Año: | 2010 |
| Volumen: | 23 |
| Número: | 10 |
| Página de inicio: | 944 |
| Página de fin: | 949 |
| DOI: | http://dx.doi.org/10.1002/poc.1732 |
| Título revista: | Journal of Physical Organic Chemistry |
| Título revista abreviado: | J Phys Org Chem |
| ISSN: | 08943230 |
| CODEN: | JPOCE |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_08943230_v23_n10_p944_Calandra |
Referencias:
- Langner, A., Panarello, A., Rivilio, S., Vassylyev, O., Khinast, J.G., Chabal, Y.J., (2005) J. Am. Chem. Soc., 127, p. 12798
- Schmeltzer, J.M., Porter Jr., L., Stewart, M.P., Buriak, J.M., (2002) Langmuir, 18, p. 2971
- Stewart, M.P., Buriak, J.M., (2001) J. Am. Chem. Soc., 123, p. 7821
- Yasuda, H., Uenoyama, Y., Nobutta, O., Kobayashi, S., Ryu, I., (2008) Tetrahedron Lett., 49, p. 367
- Marcinec, B., (1992) Comprehensive Handbook on Hydrosilylation, , Pergamon Press, Oxford
- Marciniec, B., (2002) Silicon Chem., 1, pp. 155-165
- Ojima, I., Li, Z., Zu, J., (1998) The Chemistry of Organic Silicon Compounds, 2. , (Eds.: Z. Rappoport, Y. Apeloig,) Wiley, Chichester
- Chatgilialoglu, C., (2004) Organosilanes in Radical Chemistry, , Wiley, Chicheter
- Amreim, S., Timmermann, A., Studer, A., (2001) Org. Lett., 3, p. 2357
- Postigo, A., Ferreri, C., Navacchia, M.L., Chatgilialoglu, C., (2005) Synlett, 2854
- Postigo, A., Kopsov, S., Ferreri, C., Chatgilialoglu, C., (2007) Org. Lett., 9, p. 5159
- Postigo, A., Kopsov, S., Zlotsky, S., Ferreri, C., Chatgilialoglu, C., (2009) Orga-nometallics, 28 (11), p. 3282
- Kopping, B., Chatgililaloglu, C., Zehnder, M., Giese, B., (1992) J. Org. Chem., 57, p. 3994
- Ballestri, M., Chatgilialoglu, C., Clark, K.B., Griller, D., Giese, B., Kopping, B., (1991) J. Org. Chem., 56, p. 578
- Trost, B.M., Ball, Z.T., Laemmhold, K.M., (2005) J. Am. Chem. Soc., 127, p. 10028
- Studer, A., Steen, H., (1999) Chem. Eur. J., 5 (2), p. 759
- Liu, Y., Yamazaki, S., Yamabe, S., (2005) J. Org. Chem., 70, p. 556
- Liu, Y., Yamazaki, S., Yamabe, S., Nakato, Y., (2005) J. Mater. Chem., 15, p. 4906
- Liu, Y., Yamazaki, S., Izuhara, S., (2006) J. Organomet. Chem., 691, p. 5821
- Wang, J., Zhu, Z., Huang, W., Deng, M., Zhou, X., (2008) J. Organomet. Chem., 693, p. 2188
- Postigo, A., Nudelman, N.S., J. Phys. Org. Chem., , DOI:10.1002/poc.1703
- Calandra, J., Russo, D., Tereñ, J.J., (2009), Thesis, Facultad de Ciencias Exactas y Naturales, Unversidad de Belgrano, Buenos Aires, Argentina; Miura, K., Oshima, K., Utimoto, K., (1993) Bull. Chem. Soc. Jpn., 66, p. 2356
- Postigo, A., (2009) Curr. Org. Chem., 13 (17), p. 1683
- Postigo, A., Photochemical generation of silicon-centered radicals and their reactions (2008) Progress in Photochemistry Nova Science, pp. 193-226. , ISBN 978-1-60456-568-3. Chapter VI Publications, Hauppauge, New York
- Odedra, A., Geyer, K., Gustafsson, T., Gilmour, R., Seeberger, P.H., (2008) Chem. Commun., 3025
Citas:
---------- APA ----------
Calandra, J., Postigo, A., Russo, D., Nudelman, N.S. & Tereñas, J.J. (2010) . Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: Thermal and photochemical initiation. Journal of Physical Organic Chemistry, 23(10), 944-949.http://dx.doi.org/10.1002/poc.1732
---------- CHICAGO ----------
Calandra, J., Postigo, A., Russo, D., Nudelman, N.S., Tereñas, J.J. "Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: Thermal and photochemical initiation" . Journal of Physical Organic Chemistry 23, no. 10 (2010) : 944-949.http://dx.doi.org/10.1002/poc.1732
---------- MLA ----------
Calandra, J., Postigo, A., Russo, D., Nudelman, N.S., Tereñas, J.J. "Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: Thermal and photochemical initiation" . Journal of Physical Organic Chemistry, vol. 23, no. 10, 2010, pp. 944-949.http://dx.doi.org/10.1002/poc.1732
---------- VANCOUVER ----------
Calandra, J., Postigo, A., Russo, D., Nudelman, N.S., Tereñas, J.J. Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: Thermal and photochemical initiation. J Phys Org Chem. 2010;23(10):944-949.http://dx.doi.org/10.1002/poc.1732
