Non-biaryl atropisomers derived from carbohydrates.: Part 2.: Atropisomeric behavior of monocyclic and bicyclic imidazolidine-2-ones and 2-thiones

被引：14

作者：

Avalos, M ^{[1
]}

Babiano, R

Cintas, P

Higes, FJ

Jiménez, JL

Palacios, JC

Silvero, G

Valencia, C

机构：

[1] Univ Extremadura, Fac Ciencias, Dept Quim Organ, E-06071 Badajoz, Spain

[2] Univ Extremadura, Fac Ciencias, Dept Quim Inorgan, E-06071 Badajoz, Spain

[3] Univ Extremadura, Fac Ciencias, Serv Difracc Rayos X, E-06071 Badajoz, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 14期

关键词：

atropisomerism; carbohydrates; imidazolidines; molecular mechanics; rotational isomers;

D O I：

10.1016/S0040-4020(99)00110-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High-yielding syntheses of bicyclic imidazolidine-2-ones and 2-thiones bearing an ortho-substituted aromatic ring have been described. Their atropisomeric behavior has been studied in depth taking into account the effects of substituents in the ortho position, the length of the exocyclic C=X bond, and the presence of substituents at C-5 in the heterocyclic ring. The barriers to rotation were independently estimated by dynamic NMR spectroscopy and molecular mechanics. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4401 / 4426

页数：26

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