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Abstract:

(Chemical Equation Presented) Herein we report a study involving the homogeneous catalytic reduction of unsaturated substrates in aqueous solutions or water-organic solvent mixtures. The reduction of olefins has been carried out in the presence of catalytic amounts of [Fe(CN)5NH3] 3- and excess of NH2OH, which under mild reaction conditions can be used to reduce carbon-carbon unsaturations without affecting carbonyl functionalities and aromatic rings. To explore the scope of the catalytic reduction, a wide variety of representative unsaturated substrates have been examined. The steric effects of the substituents on the carbon-carbon multiple bond as well as the regioselectivity and stereoselectivity of the catalyst have been studied. The deuterium kinetic isotope effect on the catalytic reduction of double bonds in olefins has been analyzed, and no significant kinetic isotope effect was found. Among the great advantages of this novel procedure for catalytic reduction are that hydrogen and high pressures are not needed, the catalyst is inexpensive and easily prepared, and water as well as water-organic solvent mixtures can be used as reaction media. © 2008 American Chemical Society.

Registro:

Documento: Artículo
Título:Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions
Autor:Gaviglio, C.; Doctorovich, F.
Filiación:Departamento de Quimica Inorganica, Analitica Y Quimica Fisica/INQUIMAE-CONICET, Facultad de Ciencias Exactas Y Naturales, Pabellón II, (C1428EHA) Buenos Aires, Argentina
Palabras clave:Chemical reactions; Hydrogen; Iron; Nonmetals; Olefins; Organic compounds; Organic solvents; Aqueous solutions; Catalytic amounts; Catalytic reductions; Chemical equations; Water-organic solvent mixtures; Solutions; alkene derivative; carbon; hydrogen; isotope; organic solvent; water; aqueous solution; article; catalysis; chemical reaction; cost; kinetics; pressure; reduction kinetics; stereospecificity
Año:2008
Volumen:73
Número:14
Página de inicio:5379
Página de fin:5384
DOI: http://dx.doi.org/10.1021/jo800302v
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:carbon, 7440-44-0; hydrogen, 12385-13-6, 1333-74-0; water, 7732-18-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v73_n14_p5379_Gaviglio

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Citas:

---------- APA ----------
Gaviglio, C. & Doctorovich, F. (2008) . Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions. Journal of Organic Chemistry, 73(14), 5379-5384.
http://dx.doi.org/10.1021/jo800302v
---------- CHICAGO ----------
Gaviglio, C., Doctorovich, F. "Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions" . Journal of Organic Chemistry 73, no. 14 (2008) : 5379-5384.
http://dx.doi.org/10.1021/jo800302v
---------- MLA ----------
Gaviglio, C., Doctorovich, F. "Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions" . Journal of Organic Chemistry, vol. 73, no. 14, 2008, pp. 5379-5384.
http://dx.doi.org/10.1021/jo800302v
---------- VANCOUVER ----------
Gaviglio, C., Doctorovich, F. Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions. J. Org. Chem. 2008;73(14):5379-5384.
http://dx.doi.org/10.1021/jo800302v