2-OXAZOLIDONE FORMATION BY PYROLYSIS OF BETA-IODOCARBAMATES . A STEREOSELECTIVE REACTION

被引：69

作者：

FOGLIA, TA

SWERN, D

机构：

[1] Fels Research Institute, Department of Chemistry, Temple University, Philadelphia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 06期

关键词：

D O I：

10.1021/jo01258a032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The pyrolytic cyclization of threo- and erythro-β-iodocarbamates from cis- and trans-2-butenes and -3-hexenes to 2-oxazolidones has been studied. The reaction is stereoselective, not stereospecific as with β-iodocarbamates from cyclic olefins. Selectivity of cyclization is greater with erythro than with threo isomers. The former yield 80-90% trans- and 10-20% cis-2-oxazolidones, the latter 70% cis and 30% trans. Ratios of isomers formed were determined by comparison of their nmr spectra with those of model 2-oxazolidones of known geometry. © 1969, American Chemical Society. All rights reserved.

引用

页码：1680 / &

共 20 条

[1] ELIMINATION AND REPLACEMENT REACTIONS OF DL-ERYTHRO-2-DEUTERO-1,2 DIPHENYLETHANOL AND DL-THREO-2-DEUTERO-1,2-DIPHENYLETHANOL AND DERIVATIVES [J].