Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzo-furan-1-ylidene)malonate
Artikel i vetenskaplig tidskrift, 2017

The reaction of diethyl malonate with phthaloyl chloride in acetonitrile in the presence of triethylamine and magnesium chloride results in the formation of the title compound, diethyl 2-(3-oxo-1,3-dihydro-2-benzofuran-1-ylidene)propanedioate, C15H14O6. One of the ester groups of the diethyl malonate fragment is almost coplanar with the isobenzofuran unit, while the plane of the other group is perpendicular to it [dihedral angles = 5.45 (3) and 83.30 (3)degrees, respectively]. The C-C and C-O distances both in the heterocyclic furan ring and the diethyl malonate fragment are indicative of the dipolar delocalization occurring within the isobenzofuran unit. This delocalization is likely to be responsible for the unusual intermolecular O center dot center dot center dot O contact [2.756 (2) angstrom], established between the O atom of the furan ring and the carbonyl O atom of the diethyl malonate fragment. In the crystal, weak C-H center dot center dot center dot O interactions are observed, which link the molecules into [100] chains.

acylation

Författare

Mikhail S Tyumentsev

Chalmers, Kemi och kemiteknik, Energi och material, Kärnkemi

Mark Foreman

Chalmers, Kemi och kemiteknik, Energi och material, Kärnkemi

Britt-Marie Steenari

Chalmers, Kemi och kemiteknik, Energi och material, Kärnkemi

Alexandra M. Z. Slawin

Acta Crystallographica Section E: Crystallographic Communications

2056-9890 (eISSN)

Vol. 73 10 1576-

Ämneskategorier

Kemi

DOI

10.1107/S2056989017013962