SYNTHESIS AND NMR-STUDIES OF CHIRAL 4-OXAZOLIDINONES AND RHODANINES

被引：23

作者：

DOGAN, I ^{[1
]}

BURGEMEISTER, T ^{[1
]}

ICLI, S ^{[1
]}

MANNSCHRECK, A ^{[1
]}

机构：

[1] AEGEAN UNIV,DEPT CHEM,BORNOVA,TURKEY

来源：

TETRAHEDRON | 1992年 / 48卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(01)88256-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sterically hindered N-(o-tolyl) and N-(o-chlorophenyl) substituted 2-thioxo-4-oxazolidinones 1 and-thiazolidinones (rhodanines) 2 forming enantiomers by partial rotation around the C-N bond are synthesized. Their chirality is proven by the presence of diastereotopic protons (or carbon atoms) detected by H-1 or C-13 NMR (1c, 2c). In the presence of (S)-(+)-1-(9-anthryl)-2,2,2-trifluoroethanol as an auxiliary the enantiomers showed H-1 shift differences of 0.01 ppm for otherwise isochronous nuclei.

引用

收藏

页码：7157 / 7164

页数：8

相关论文

共 16 条

[1] AN X-RAY-ANALYSIS ON RESTRICTED ROTATIONAL ISOMERS OF 2-THIOXO-4-OXAZOLIDINONE [J].

AKSAC, Z ;

ICLI, S ;

KRUGER, C ;

TSAY, CY .

SPECTROSCOPY LETTERS, 1983, 16 (09) :683-692

[2] H-1 AND C-13 NMR-STUDIES ON 3-ARYL-2-THIOXO-4-OXAZOLIDINONES AND 3-ARYLRHODANINES [J].

AKSAC, Z ;

PINAR, E ;

ICLI, S .

ORGANIC MAGNETIC RESONANCE, 1983, 21 (09) :548-551

[3]

ANDREASCH R, 1905, MONATSH CHEM, V26, P725

[4] HINDERED ROTATION ABOUT C-N BONDS - EQUILIBRATION OF DIASTEREOMERIC ROTATIONAL ISOMERS [J].

BENTZ, WE ;

COLEBROO.LD ;

FEHLNER, JR ;

ROSOWSKY, A .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (16) :974-&

[5] CONFORMATIONAL PREFERENCES IN SOME ARYL SUBSTITUTED HETEROCYCLIC-COMPOUNDS EXHIBITING RESTRICTED INTERNAL-ROTATION ABOUT C-N BONDS [J].

BIRD, PH ;

COLEBROO.LD ;

FRASER, AR ;

GILES, HG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (06) :225-226

[6] SOME 3-SUBSTITUTED RHODANINES [J].

BROWN, FC ;

BRADSHER, CK ;

MORGAN, EC ;

TETENBAUM, M ;

WILDER, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (02) :384-388

[7]

BURGMEISTER T, UNPUB

[8]

Cahn R. S., 1966, ANGEW CHEM, V78, P413, DOI DOI 10.1002/ANGE.19660780803

[9] SPECIFICATION OF MOLECULAR CHIRALITY [J].

CAHN, RS ;

INGOLD, C ;

PRELOG, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (04) :385-&

[10] RESTRICTED INTERNAL-ROTATION IN 1-ARYLHYDANTOINS, 3-ARYLHYDANTOINS, AND 3-ARYL-2-THIOHYDANTOINS - REVERSAL OF EFFECTIVE SIZES OF METHYL AND CHLORINE [J].

COLEBROOK, LD ;

GILES, HG ;

GRANATA, A ;

ICLI, S ;

FEHLNER, JR .

CANADIAN JOURNAL OF CHEMISTRY, 1973, 51 (21) :3635-3639