Synthesis, structure and AM1 conformational study of 1,12-dioxa-2,11-dioxo[3.3]orthocyclophane

Autor: Bodwell, Graham J., Houghton, Tom J., Miller, David
Zdroj: Tetrahedron Letters; January 1997, Vol. 38 Issue: 9 p1469-1472, 4p
Abstrakt: The title compound was synthesized by a two-fold BOP-Cl mediated esterification of o-phenylenediacetic acid with catechol. The presence of the bridging esters results in a considerable change in the conformational landscape of the cyclophane system in comparison to the parent [3.3]orthocyclophane and related systems. A conformer search at the AM1 level identified six low energy conformers. The one observed in the solid state was calculated to be the second lowest in energy, 0.32 kcal/mol above the calculated global minimum.
Databáze: Supplemental Index