Crystallographic identification of an unexpected by-product in an Ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone

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 N...

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Autores principales:	Manzano, V.E., Baggio, R., Cukiernik, F.D.
Formato:	JOUR
Materias:	1-(4-hexyloxy-3-hydroxyphenyl)ethanone biphenyls chemical identification crystal structure Ni-modified Ullmann reaction rearrangement Nickel Nuclear magnetic resonance spectroscopy Single crystals Chemical identification Ullmann reaction Crystal structure
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_20532296_v71_n_p1022_Manzano
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_20532296_v71_n_p1022_Manzano
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spelling	todo:paper_20532296_v71_n_p1022_Manzano2023-10-03T16:39:00Z Crystallographic identification of an unexpected by-product in an Ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone Manzano, V.E. Baggio, R. Cukiernik, F.D. 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 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. Fil:Manzano, V.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Cukiernik, F.D. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_20532296_v71_n_p1022_Manzano
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	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
spellingShingle	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 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
topic_facet	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
description	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.
format	JOUR
author	Manzano, V.E. Baggio, R. Cukiernik, F.D.
author_facet	Manzano, V.E. Baggio, R. Cukiernik, F.D.
author_sort	Manzano, V.E.
title	Crystallographic identification of an unexpected by-product in an Ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone
title_short	Crystallographic identification of an unexpected by-product in an Ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone
title_full	Crystallographic identification of an unexpected by-product in an Ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone
title_fullStr	Crystallographic identification of an unexpected by-product in an Ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone
title_full_unstemmed	Crystallographic identification of an unexpected by-product in an Ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone
title_sort	crystallographic identification of an unexpected by-product in an ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone
url	http://hdl.handle.net/20.500.12110/paper_20532296_v71_n_p1022_Manzano
work_keys_str_mv	AT manzanove crystallographicidentificationofanunexpectedbyproductinanullmansreactiontowardbiphenyls14hexyloxy3hydroxyphenylethanone AT baggior crystallographicidentificationofanunexpectedbyproductinanullmansreactiontowardbiphenyls14hexyloxy3hydroxyphenylethanone AT cukiernikfd crystallographicidentificationofanunexpectedbyproductinanullmansreactiontowardbiphenyls14hexyloxy3hydroxyphenylethanone
_version_	1807324556212305920

Crystallographic identification of an unexpected by-product in an Ullman's reaction toward biphenyls: 1-(4-hexyloxy-3-hydroxyphenyl)ethanone

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