Artículo

La versión final de este artículo es de uso interno. El editor solo permite incluir en el repositorio el artículo en su versión post-print. Por favor, si usted la posee enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

The reactions of aryllithium compounds (Ar= phenyl, 1-naphthyl, xylyl, mesityl) with CO have been studied under several reaction conditions. A 13C NMR method developed to determine radicals at preparative concentrations revealed the presence of radical anions in the reaction mixtures in concentrations comparable to those of the reagents. ESR spectroscopic studies, the effect of radical inhibitors, kinetic measurements and isolation of derivatives of some intermediates suggest a mechanism that involves electron transfer as the first and rate determining step of the reaction. © 1993.

Registro:

Documento: Artículo
Título:Electron transfer in the reactions of aryllithium compounds with carbon monoxide
Autor:Nudelman, N.S.; Doctorovich, F.
Filiación:Depto. Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pab. II, P. 3, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:alkanediol derivative; ketone; organolithium compound; organometallic compound; article; nuclear magnetic resonance; priority journal; reaction analysis; synthesis
Año:1994
Volumen:50
Número:16
Página de inicio:4651
Página de fin:4666
DOI: http://dx.doi.org/10.1016/S0040-4020(01)85005-5
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v50_n16_p4651_Nudelman

Referencias:

  • Fox, Introduction - Electron Transfer: A Critical Link between Subdisciplines in Chemistry (1992) Chemical Reviews, 92, p. 365
  • Eberson, (1992) New J. Chem., 16, p. 151
  • Bolton, Mataga, McLendon, (1991) Electron Transfer in Inorganic, Organic, and Biological Systems, , ACS, Washington, D. C, Adv. Chem. Series 228
  • Eberson, (1987) Electron Transfer Reactions in Organic Chemistry, , Springer, Berlin and Heidelberg
  • Fox, (1988) Photoinduced Electron Transfer, , M. Chanon, Elsevier, Amsterdam
  • Ashby, (1988) Acc. Chem. Res., 21, p. 414
  • Newcomb, Curran, (1988) Acc. Chem. Res., 21, p. 206
  • Ashby, Pham, (1987) J. Org. Chem., 52, p. 1292
  • Ashby, Coleman, Gamasa, (1987) J. Org. Chem., 52, p. 4079
  • Sato, Wakahara, Otera, Noyaki, (1991) J. Am. Chem. Soc., 113, p. 4028
  • Beckwith, Bowry, Ingold, (1992) J. Am. Chem. Soc., 114, p. 4983
  • Bowry, Ingold, (1992) J. Am. Chem. Soc., 114, p. 4992
  • Bockman, Karpinski, Sankararaman, Kochi, (1992) J. Am. Chem. Soc., 114, p. 1970
  • Bockman, Karpinski, Sankararaman, Kochi, (1991) J. Am. Chem. Soc., 113, p. 4962
  • Bordwell, Wilson, (1987) J. Am. Chem. Soc., 109, p. 5465
  • Saveant, (1992) New J. Chem., 16, p. 131
  • Poli, Owens, Linck, (1992) J. Am. Chem. Soc., 114, p. 1302
  • Andrieux, Hapiot, Saveant, (1990) Chem. Rev., 90, p. 113
  • Evans, (1990) Chem. Rev., 90, p. 739
  • Chanon, Tobe, (1982) Angew. Chem. Int. Ed. Engl., 21, p. 1
  • Cho, Shaik, (1991) J. Am. Chem. Soc., 113, p. 9890
  • Shaik, The SN2 and Single Electron Transfer Concepts. A Theoretical and Experimental Overview. (1990) Acta Chemica Scandinavica, 44, p. 205
  • Newton, (1991) Chem. Rev., 91, p. 767
  • Eberson, Shaik, (1990) J. Am. Chem. Soc., 112, p. 4489
  • Purcell, Blaive, Theory of Electron Transfer Reactions (1988) Photoinduced Electron Transfer, , M.A. Fox, M. Chanon, Elsevier, Amsterdam, Part A
  • Shaik, The Collage of SN2 Reactivity Patterns: A State Correlation Diagram Model (1985) Prog. Phys. Org. Chem., 15, p. 197
  • Pross, (1985) Acc. Chem. Res., 18, p. 212
  • Pross, (1985) Adv. Phys. Org. Chem., 21, p. 99
  • Nishiyama, Katsuura, Negoro, Hamanaka, Miyoshi, Yamana, Ogawa, Sonoda, (1991) J. Org. Chem., 56, p. 3776
  • Ryu, Kusano, Yamazaki, Sonoda, (1991) J. Org. Chem., 56, p. 5003
  • Ryu, Kusano, Ogawa, Kambe, Sonoda, (1990) J. Am. Chem. Soc., 112, p. 1295
  • Protasiewicz, Lippard, (1991) J. Am. Chem. Soc., 113, p. 6564
  • Dufaud, Thivolle-Cazat, Basset, Mathieu, Jaud, Waissermann, (1991) Organometallics, 10, p. 4005
  • Chen, Tzeng, Tsai, Cheng, Wang, (1991) Organometallics, 10, p. 3954
  • Moloy, Fagan, Manriquez, Marks, (1986) J. Am. Chem. Soc., 108, p. 56
  • Marks, Day, (1985) Fundamental and Technological Aspects of Organo-f-Element Chemistry, pp. 115-157. , T.J. Marks, I.L. Fragala, Reidel, Dordrecht
  • Nudelman, Carbonylation of Main-Group Organometallic Compounds (1989) The Chemistry of Double Bonded Functional Groups, , S. Patai, Z. Rappoport, Wiley, Chichester, ch. 13
  • Seyferth, Hui, Weinstein, Wang, (1985) Nova Acta Leopoldina, 9, p. 335. , and refs. therein
  • Nudelman, Lewkowicz, Perez, One-Pot Synthesis ofN,N,N′,N′-Tetrasubstituted Ureas and Oxomalonamides by Oxidative Carbonylation of Lithium Amides at Atmospheric Pressure (1990) Synthesis, p. 917
  • Nudelman, N. S.; Lewkowicz, E. S.; Furlong, J. P. J.; in press; Perez, Nudelman, Carbon-carbon bond formation through the carbonylation of lithium dialkylamides. One-pot synthesis of N-alkyl-substituted formamides, glyoxylamides, and hydroxymalonamides (1988) The Journal of Organic Chemistry, 53, p. 408
  • Trzupek, Newirth, Kelly, Nudelman, Whitesides, (1973) J. Am. Chem. Soc., 95, p. 8118
  • Nudelman, Doctorovich, Amorin, (1990) Tetrahedron Lett., 31, p. 2553
  • Doctorovich, Nudelman, 13C NMR studies on radical anions. Special solvent effects (1990) Magnetic Resonance in Chemistry, 28, p. 576
  • Nudelman, Outumuro, (1982) J. Org. Chem., 47, p. 4347
  • Nudelman, Vitale, (1983) J. Organometal. Chem., 241, p. 143
  • Nudelman, Vitale, A CONVENIENT PREPARATION OF α,α-DIPHENYLACETOPHENONE (1981) Organic Preparations and Procedures International, 13, p. 144
  • Vitale, Doctorovich, Nudelman, (1987) J. Organometal. Chem., 332, p. 9
  • Nudelman, Vitale, (1981) J. Org. Chem., 46, p. 4625
  • Ashby, Argyropoulos, (1986) J. Org. Chem., 51, p. 472
  • Ashby, De Priest, Su, (1984) Organometallics, p. 1718
  • Newcomb, Sanchez, Kaplan, (1987) J. Am. Chem. Soc., 109, p. 1195
  • Newcomb, Burchill, (1984) J. Am. Chem. Soc., 106, p. 8276
  • Screttas, Micha-Screttas, (1983) J. Phys. Chem., 87, p. 3844
  • Doesher, Wheland, MAGNETIC SUSCEPTIBILITY OF METAL KETYLS (1934) Journal of the American Chemical Society, 56, p. 2011
  • Joela, A microcomputer program for second-order simulation of EPR spectra (1987) Computers & Chemistry, 12, p. 189
  • Maruyama, Katagiri, Mechanism of the Grignard reaction (1989) Journal of Physical Organic Chemistry, 2, p. 205
  • Maruyama, Katagiri, Structure of radical intermediates appearing in the grignard reaction of monoketones (1988) Journal of Physical Organic Chemistry, 1, p. 21
  • Maruyama, Katagiri, (1986) J. Am. Chem. Soc., 108, p. 6263
  • Nudelman, N. S.; Doctorovich, Fabio; in preparation; Capek, Barton, (1985) Die Makromolekulare Chemie, 186, p. 1297
  • Arnoldi, Citterio, Minisci, Electron-transfer processes: metal salt catalysed oxidation of olefins by peroxydisulphate (1983) Journal of the Chemical Society, Perkin Transactions 2, p. 531
  • Rak, Miller, (1992) J. Am. Chem. Soc., 114, p. 1388
  • Hanhela, Paul, Synthesis and evaluation of fluorescent materials for colour control of peroxyoxalate chemiluminescence. III. Yellow and red fluorescent emitters (1970) Australian Journal of Chemistry, 34, p. 1701
  • Moore, Sing, Sidhu, (1977) J. Org. Chem., 42, p. 3320
  • Yamataka, Fujimura, Kawafuji, Hanafusa, (1987) J. Am. Chem. Soc., 109, p. 4305
  • Yamataka, Matsuyama, Hanafusa, Kinetic isotope effect and substituent effect study on the Grignard reaction of MeMgI with benzophenone. A rate-determining C-C bond formation. (1987) Chemistry Letters, p. 647
  • Matsuyama, Yamataka, Hanafusa, Rate-determining electron transfer from allylic Grignard reagents to benzophenone. (1988) Chemistry Letters, p. 1367
  • Buchner, Zur Kenntnis der sogenannten „Alkalicarbonyle”, IX. Untersuchung der Reduktion von Kohlenmonoxid durch aromatische Radikal-Anionen (1966) Chemische Berichte, 99, p. 1485
  • Rizkallc, Goliaszewski, Production of Vinyl Acetate from Methanol and Synthesis Gas (1987) ACS Symposium Ser., 328, p. 136
  • Prent, Production of Ethyl Acetate and Propionic Acid from Methanol and Synthesis Gas (1987) ACS Symposium Ser., 328, p. 154
  • Rempt, Electron-Impact Excitation of Carbon Monoxide Near Threshold in the 1.5- to 3-eV Incident Energy Range (1969) Physical Review Letters, 22, p. 1034
  • Yamataka, Matsuyama, Hanafusa, (1989) J. Am. Chem. Soc., 111, p. 4912
  • Yamataka, Kawafuji, Nagareda, Miyano, Hanafusa, (1989) J. Org. Chem., 54, p. 4706
  • Okubo, Matsuo, Organomagnesium Reagents. Single Electron Transfer Efficiency and Systematic Characterization of Reactions of C-Mg and N-Mg Reagents. (1992) Journal of Synthetic Organic Chemistry, Japan, 50, p. 682
  • Stevenson, Hashim, (1985) J. Am. Chem. Soc., 107, p. 5794
  • Hiiro, Morita, Inoue, Kambe, Ogawa, Ryu, Sonoda, (1990) J. Am. Chem. Soc., 112, p. 455
  • Moloy, Marks, Day, (1983) J. Am. Chem. Soc., 105, p. 5696
  • Sonnenberger, Mintz, Marks, (1984) J. Am. Chem. Soc., 106, p. 3484
  • Berg, Petersen, (1991) Organometallics, 10, p. 1599
  • Hoffmann, Wilker, Lippard, Templeton, Brower, (1983) J. Am. Chem. Soc., 105, p. 146
  • Boche, Opel, Marsch, Harms, Haller, Lohrenz, Thummler, Koch, α-Oxygen-Substituted Organolithium Compounds and Their Carbenoid Nature: Calculations of the Configurational Stability and of LiCH2OH Model Structures, Crystal Structure of Diphenyl(trimethylsilyloxy)methyllithium · 3 THF, and the Stereochemistry of the (Reverse) Brook Rearrangement (1992) Chemische Berichte, 125, p. 2265
  • Boche, Marsch, Muller, Harms, (1993) Angew. Chem. Int. Ed. Engl., 32, p. 1032
  • Walling, A fresh look at electron transfer in the reactions of Grignard reagents (1988) Journal of the American Chemical Society, 110, p. 6845
  • Scaiano, Stewart, (1983) J. Am. Chem. Soc., 105, p. 3609
  • Bakac, Espenson, Kinetics of the capture of methyl radicals by carbon monoxide in aqueous solution (1991) Journal of the Chemical Society, Chemical Communications, p. 1497
  • Garst, Smith, (1976) J. Am. Chem. Soc., 98, p. 1520
  • Carloni, Greci, Stipa, Eberson, (1991) J. Org. Chem., 56, p. 4733
  • Mondodoev, Przhiyalgouskaya, Belov, (1965) Zh. Org. Khim., 1, p. 2008
  • Schmidlin, Massini, (1909) Ber., 42, p. 2388
  • Kohler, Baltzly, (1932) J. Am. Chem. Soc., 54, p. 4015
  • Sass, Ziessow, (1977) J. Magn. Res., 25, p. 263
  • Swift, (1973) NMR of Paramagnetic Molecules, pp. 53-83. , G.N. La Mar, W.D. Harrocks, R.H. Holm, Academic Press, New York
  • Allinger, Yuh, (1980) QCPE, 12, p. 395
  • Allinger, (1977) J. Am. Chem. Soc., 99, p. 8127
  • Propheta, Jr., (1981) QCPE Bull., 1, p. 57
  • Shriver, (1989) The Manipulation of Air Sensitive Compounds, , Wiley, N. Y

Citas:

---------- APA ----------
Nudelman, N.S. & Doctorovich, F. (1994) . Electron transfer in the reactions of aryllithium compounds with carbon monoxide. Tetrahedron, 50(16), 4651-4666.
http://dx.doi.org/10.1016/S0040-4020(01)85005-5
---------- CHICAGO ----------
Nudelman, N.S., Doctorovich, F. "Electron transfer in the reactions of aryllithium compounds with carbon monoxide" . Tetrahedron 50, no. 16 (1994) : 4651-4666.
http://dx.doi.org/10.1016/S0040-4020(01)85005-5
---------- MLA ----------
Nudelman, N.S., Doctorovich, F. "Electron transfer in the reactions of aryllithium compounds with carbon monoxide" . Tetrahedron, vol. 50, no. 16, 1994, pp. 4651-4666.
http://dx.doi.org/10.1016/S0040-4020(01)85005-5
---------- VANCOUVER ----------
Nudelman, N.S., Doctorovich, F. Electron transfer in the reactions of aryllithium compounds with carbon monoxide. Tetrahedron. 1994;50(16):4651-4666.
http://dx.doi.org/10.1016/S0040-4020(01)85005-5