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

被引：13

作者：

Bodwell, GJ

Houghton, TJ

Miller, D

机构：

[1] Chemistry Department, Memorial University of Newfoundland, St. John's

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 09期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4039(97)00132-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound was synthesized by a two-fold BOP-CI 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 AMI 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. (C) 1997 Elsevier Science Ltd.

引用

页码：1469 / 1472

页数：4

共 12 条

[1] TRANS-ANNULAR BROMINOLYSIS OF 5,7,12,14-TETRAHYDRODIBENZO[C,H][1,6]DITHIECINS BY PYRIDINIUM HYDROBROMIDE PERBROMIDE [J].