CONFORMATIONAL DYNAMIC INVESTIGATION OF 1,5-BENZODIOXEPIN AND ITS DIMETHYL DERIVATIVE BY H-1 AND C-13 NMR

被引：20
|
作者：
MENARD, D
STJACQUES, M
机构：
来源：
CANADIAN JOURNAL OF CHEMISTRY | 1981年 / 59卷 / 07期
关键词：
D O I：
10.1139/v81-170
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The conformational and dynamic properties of 1,5-dioxa-6,7-benzocycloheptene (2; 1,5-benzodioxepine) and its dimethyl derivative (7) were investigated by dynamic 1H and 13C NMR methods. Analysis of the spectra at low temperatures (below coalescence) indicates that the most stable 7-membered ring conformations detected for solutions in CHF2Cl are a mixture of the chair (C, 80%) and the twist-boat (TB, 20%) for 2 and a mixture of TB (64%) and C (36%) for 7. Free energy barriers were determined for the chair inversion of 2 (6.5 kcal/mol) and 7 (7.5 kcal/mol) and for the TB pseudorotation of 7 (6.8 kcal/mol). The conformational properties of these 7-membered heterocycles are discussed and compared to those known for 2,4-benzodioxepines.
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页码：1160 / 1168
页数：9
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