SYNTHESIS, STRUCTURE AND AM1 CONFORMATIONAL STUDY OF 1,12-DIOXA-2,11-DIOXO[3.3]ORTHOCYCLOPHANE

Authors
BODWELL GJ HOUGHTON TJ MILLER D
Citation
Gj. Bodwell et al., SYNTHESIS, STRUCTURE AND AM1 CONFORMATIONAL STUDY OF 1,12-DIOXA-2,11-DIOXO[3.3]ORTHOCYCLOPHANE, Tetrahedron letters, 38(9), 1997, pp. 1469-1472
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
9
Year of publication
1997
Pages
1469 - 1472
Database
ISI
SICI code
0040-4039(1997)38:9<1469:SSAACS>2.0.ZU;2-5
Abstract
The title compound was synthesized by a two-fold BOP-CI mediated ester ification of o-phenylenediacetic acid with catechol. The presence of t he bridging esters results in a considerable change in the conformatio nal landscape of the cyclophane system in comparison to the parent [3. 3]orthocyclophane and related systems. A conformer search at the AMI l evel identified six low energy conformers. The one observed in the sol id state was calculated to be the second lowest in energy, 0.32 kcal/m ol above the calculated global minimum. (C) 1997 Elsevier Science Ltd.