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Abstract:

The synthesis of 3,3′-diacetoxy-4,4′-bis(hexyloxy)biphenyl following the nickel-modified Ullmann reaction yielded a by-product which was identified successfully by crystallographic analysis as 1-(4-hexyloxy-3-hydroxyphenyl)ethanone, C14H20O3. This unexpected nonbiphenyl by-product exhibited IR, 1H NMR, 13C NMR and COSY (correlation spectroscopy) spectra fully consistent with the proposed structure. The compound crystallized in the orthorombic Pbca space group, with two independent formula units in the asymmetric unit (one of which was slightly disordered), and showed a supramolecular architecture in which molecules linked by hydroxy-ethanone O - H⋯O interactions are organized in columns separated by the aliphatic tails. © 2015 International Union of Crystallography.

Registro:

Documento: Artículo
Título:Crystallographic identification of an unexpected by-product in an Ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone
Autor:Manzano, V.E.; Baggio, R.; Cukiernik, F.D.
Filiación:Departamento de Química Inorgánica, Analítica y Química Física/INQUIMAE-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina
Gerencia de Investigación y Aplicaciones, Centro Atómico Constituyentes, Comisión Nacional de Energía Atómica, Buenos Aires, Argentina
Palabras clave:1-(4-hexyloxy-3-hydroxyphenyl)ethanone; biphenyls; chemical identification; crystal structure; Ni-modified Ullmann reaction; rearrangement; Nickel; Nuclear magnetic resonance spectroscopy; Single crystals; 1-(4-hexyloxy-3-hydroxyphenyl)ethanone; biphenyls; Chemical identification; rearrangement; Ullmann reaction; Crystal structure
Año:2015
Volumen:71
Página de inicio:1022
Página de fin:1027
DOI: http://dx.doi.org/10.1107/S2053229615019919
Título revista:Acta Crystallographica Section C: Structural Chemistry
Título revista abreviado:Acta crystallogr., C Struct. Chem.
ISSN:20532296
CODEN:ACSCG
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20532296_v71_n_p1022_Manzano

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Citas:

---------- APA ----------
Manzano, V.E., Baggio, R. & Cukiernik, F.D. (2015) . Crystallographic identification of an unexpected by-product in an Ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone. Acta Crystallographica Section C: Structural Chemistry, 71, 1022-1027.
http://dx.doi.org/10.1107/S2053229615019919
---------- CHICAGO ----------
Manzano, V.E., Baggio, R., Cukiernik, F.D. "Crystallographic identification of an unexpected by-product in an Ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone" . Acta Crystallographica Section C: Structural Chemistry 71 (2015) : 1022-1027.
http://dx.doi.org/10.1107/S2053229615019919
---------- MLA ----------
Manzano, V.E., Baggio, R., Cukiernik, F.D. "Crystallographic identification of an unexpected by-product in an Ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone" . Acta Crystallographica Section C: Structural Chemistry, vol. 71, 2015, pp. 1022-1027.
http://dx.doi.org/10.1107/S2053229615019919
---------- VANCOUVER ----------
Manzano, V.E., Baggio, R., Cukiernik, F.D. Crystallographic identification of an unexpected by-product in an Ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone. Acta crystallogr., C Struct. Chem. 2015;71:1022-1027.
http://dx.doi.org/10.1107/S2053229615019919