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Abstract:

A 13C NMR method was developed for quantitative determination of radical anions in relatively high concentration and applied to the reaction of phenyllithium with carbon monoxide where those species were detected. © 1990.

Registro:

Documento: Artículo
Título:Spectroscopic determination of radical anions in the reaction of phenyllithium with carbon monoxide
Autor:Nudelman, N.S.; Doctorovich, F.; Amorin, G.
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:carbon monoxide; lithium; article; chemical structure; nonhuman; nuclear magnetic resonance; priority journal; reaction analysis
Año:1990
Volumen:31
Número:18
Página de inicio:2533
Página de fin:2536
DOI: http://dx.doi.org/10.1016/0040-4039(90)80118-6
Título revista:Tetrahedron Letters
Título revista abreviado:Tetrahedron Lett.
ISSN:00404039
CODEN:TELEA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v31_n18_p2533_Nudelman

Referencias:

  • Vitale, Doctorovich, Nudelman, (1987) J. Organometal. Chem., 332, p. 9
  • Nudelman, Vitale, (1983) J. Organometal. Chem., 241, p. 143
  • Nudelman, Vitale, (1981) J. Org. Chem., 46, p. 4625
  • Nudelman, Outumuro, (1982) J. Org. Chem., 47, p. 4347
  • Seyferth, Weinstein, Wang, Hui, Archer, Direct Nucleophilic Acylation with Acyllithium Reagents: Acyl Anion Synthons Unmasked (1984) Israel Journal of Chemistry, 24, p. 167. , and references therein
  • 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
  • Nudelman, Perez, (1983) J. Org. Chem., 48, p. 133
  • Trzupek, Newirth, Kelly, Nudelman, Whitesides, (1973) J. Am. Chem. Soc., 95, p. 8118
  • Ashby, Coleman, Evidence for single electron transfer in the reactions of lithium dimethylcuprate with alkyl halides (1987) The Journal of Organic Chemistry, 109, p. 4554
  • Yamataka, Fujimura, Kawafuji, Hanafusa, (1987) J. Am. Chem. Soc., 109, p. 4305
  • Alnajjar, Huivila, (1985) J. Am. Chem. Soc., 107, p. 416
  • Ashby, Argyropoulos, (1986) J. Org. Chem., 51, p. 472
  • 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
  • Ashby, (1988) Acc. Chem. Res., 21, p. 414
  • Ashby, Pham, (1987) J. Org. Chem., 52, p. 1291
  • Newcomb, Curran, (1988) Acc. Chem. Res., 21, p. 206
  • Newcomb, Sanchez, Kaplan, (1987) J. Am. Chem. Soc., 109, p. 1195
  • Doctorovich, F.; Nudelman, N. S. Mag. Res. Chem., submitted; Nudelman, Vitale, A CONVENIENT PREPARATION OF α,α-DIPHENYLACETOPHENONE (1981) Organic Preparations and Procedures International, 13, p. 44
  • Nudelman, Doctorovich, (1989) Proc. VI Argentine Symposium in Org. Chem.
  • Although phenyllithium is written as a monomer, aggregation of the reagent in the solvents used is well stablished. See for instance ref. 18. See also ref. 19; Nudelmam, Carbonylation of Main-Group Organometallic Compounds (1989) The Chemistry of Functional Groups, pp. 799-962. , S. Patai, Z. Rappoport, Wiley, and references therein
  • The proposed Scheme does not preclude other possible pathways to products

Citas:

---------- APA ----------
Nudelman, N.S., Doctorovich, F. & Amorin, G. (1990) . Spectroscopic determination of radical anions in the reaction of phenyllithium with carbon monoxide. Tetrahedron Letters, 31(18), 2533-2536.
http://dx.doi.org/10.1016/0040-4039(90)80118-6
---------- CHICAGO ----------
Nudelman, N.S., Doctorovich, F., Amorin, G. "Spectroscopic determination of radical anions in the reaction of phenyllithium with carbon monoxide" . Tetrahedron Letters 31, no. 18 (1990) : 2533-2536.
http://dx.doi.org/10.1016/0040-4039(90)80118-6
---------- MLA ----------
Nudelman, N.S., Doctorovich, F., Amorin, G. "Spectroscopic determination of radical anions in the reaction of phenyllithium with carbon monoxide" . Tetrahedron Letters, vol. 31, no. 18, 1990, pp. 2533-2536.
http://dx.doi.org/10.1016/0040-4039(90)80118-6
---------- VANCOUVER ----------
Nudelman, N.S., Doctorovich, F., Amorin, G. Spectroscopic determination of radical anions in the reaction of phenyllithium with carbon monoxide. Tetrahedron Lett. 1990;31(18):2533-2536.
http://dx.doi.org/10.1016/0040-4039(90)80118-6