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Crystal structure of ethyl 2-(di­eth­oxy­phosphor­yl)-2-(2,3,4-tri­meth­oxy­phen­yl)acetate

The title compound, C(17)H(27)O(8)P, was prepared by Michaelis–Arbuzov reaction of ethyl 2-bromo-2-(2,3,4-tri­meth­oxy­phen­yl)acetate and triethyl phosphite. Such compounds rarely crystallize, but single crystals were recovered after the initial oil was left for approximately 10 years. The bond ang...

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Detalles Bibliográficos
Autores principales: Schubert, Moritz, Schollmeyer, Dieter, Waldvogel, Siegfried R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4186086/
https://www.ncbi.nlm.nih.gov/pubmed/25309241
http://dx.doi.org/10.1107/S1600536814015803
Descripción
Sumario:The title compound, C(17)H(27)O(8)P, was prepared by Michaelis–Arbuzov reaction of ethyl 2-bromo-2-(2,3,4-tri­meth­oxy­phen­yl)acetate and triethyl phosphite. Such compounds rarely crystallize, but single crystals were recovered after the initial oil was left for approximately 10 years. The bond angle of the sp (3)-hybridized C atom connecting the benzene derivative with the phospho unit is widened marginally [112.5 (2)°]. The terminal P—O bond length of 1.464 (2) Å clearly indicates a double bond, whereas the two O atoms of the eth­oxy groups connected to the phospho­rous atom have bond lengths of 1.580 (2) Å and 1.581 (3) Å. The three meth­oxy groups emerge out of the benzene-ring plane due to steric hindrance [C—C—O—C torsion angles = −179.9 (3)°, −52.9 (4)° and 115.3 (4)°]. In the crystal, inversion dimers linked by pairs of C—H⋯O=P hydrogen bonds generate R (2) (2)(14) loops. The chosen crystal was modelled as a non-merohedral twin.