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Abstract:

The carbonylation of a THF solution of aryllithium (aryl = Ph, o-anisyl) in the presence of an alkyl bromide, RBr; at atmospheric pressure and -78°C, affords diarylalkylcarbinols in good yields. Alkyl chlorides do not react under similar experimental conditions. This feature makes the reaction particularly useful for the synthesis of alcohols functionalized in the alkyl chain through subsequent reactions of the diaryl(chloro)alkylcarbinols. The procedure can also be adapted to afford substituted cyclic ethers. If the reaction is carried out in the presence of dibromoalkanes, only one bromine atom reacts, affording diaryl(bromo)alkylcarbinols which are useful synthetic intermediates. With secondary and tertiary alkyl bromides diaryl alkyl ethers are obtained in variable yields. © 1987.

Registro:

Documento: Artículo
Título:One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums
Autor:Vitale, A.A.; Doctorovich, F.; Sbarbati Nudelman, N.
Filiación:Departamento Química Orgánica, Facultad de Ciencias Exactas, Universidad de Buenos Aires, Pab. II, P. 3 Ciudad Universitaria, 1428 Buenos Aires, Argentina
Año:1987
Volumen:332
Número:1-2
Página de inicio:9
Página de fin:18
DOI: http://dx.doi.org/10.1016/0022-328X(87)85117-3
Título revista:Journal of Organometallic Chemistry
Título revista abreviado:J. Organomet. Chem.
ISSN:0022328X
CODEN:JORCA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022328X_v332_n1-2_p9_Vitale

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Citas:

---------- APA ----------
Vitale, A.A., Doctorovich, F. & Sbarbati Nudelman, N. (1987) . One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums. Journal of Organometallic Chemistry, 332(1-2), 9-18.
http://dx.doi.org/10.1016/0022-328X(87)85117-3
---------- CHICAGO ----------
Vitale, A.A., Doctorovich, F., Sbarbati Nudelman, N. "One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums" . Journal of Organometallic Chemistry 332, no. 1-2 (1987) : 9-18.
http://dx.doi.org/10.1016/0022-328X(87)85117-3
---------- MLA ----------
Vitale, A.A., Doctorovich, F., Sbarbati Nudelman, N. "One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums" . Journal of Organometallic Chemistry, vol. 332, no. 1-2, 1987, pp. 9-18.
http://dx.doi.org/10.1016/0022-328X(87)85117-3
---------- VANCOUVER ----------
Vitale, A.A., Doctorovich, F., Sbarbati Nudelman, N. One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums. J. Organomet. Chem. 1987;332(1-2):9-18.
http://dx.doi.org/10.1016/0022-328X(87)85117-3