SYNTHESIS AND STEREOCHEMISTRY OF SOME NEW CHIRAL BROMINATED 1,3-DIOXANES

被引:20
作者
GROSU, I
PLE, G
MAGER, S
机构
[1] UNIV ROUEN,FAC SCI,F-76821 MONT ST AIGNAN,FRANCE
[2] IRCOF,CNRS,LAB DO464,F-76821 MONT ST AIGNAN,FRANCE
关键词
D O I
10.1016/0040-4020(94)01112-D
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereochemistry of some new 1,3-dioxanes with brominated chiral groups located in the (a)ketalic part of the heterocycle, obtained by a regioselective radicalic bromination reaction, nas investigated by NMR methods. The experiments demonstrated the fixed or flipping structures of the compounds. The influence of the chiral carbon atoms was analyzed by means of the diastereotopicity of protons and carbon atoms. In the case of polychiral compounds, the diastereoselectivity of the bromi-nation reaction was studied.
引用
收藏
页码:2659 / 2672
页数:14
相关论文
共 22 条
[1]  
ANTEUNIS MJO, 1976, HETEROCYCLES, V4, P293
[2]   DESHIELDING GAMMA-GAUCHE EFFECTS IN C-13 MAGNETIC-RESONANCE - A COMPARISON OF THE CONFORMATIONAL BEHAVIOR OF THE ACETYL GROUP IN CYCLOHEXANE AND 5-SUBSTITUTED-1,3-DIOXANE SYSTEMS [J].
BUCHANAN, GW ;
PREUSSER, SH ;
WEBB, VL .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (07) :1308-1311
[3]  
COENE E, 1970, B SOC CHIM BELG, V79, P37
[4]   NMR-SPECTRA AND STEREOCHEMISTRY OF 5,5-DISUBSTITUTED-1,3-DIOXANS [J].
CRABB, TA ;
PORSSA, M ;
ELMORE, NF .
MAGNETIC RESONANCE IN CHEMISTRY, 1991, 29 (06) :613-618
[5]   CONFORMATIONAL-ANALYSIS OF 5-ACYL-1,3-DIOXAN - H-1-NMR STUDY OF 1,3-DIOXANS SUBSTITUTED IN POSITION-5 BY AN ALIPHATIC OR AROMATIC ACYL GROUP [J].
DENIS, A ;
DELMAS, M ;
GASET, A ;
GORRICHON, JP .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (15) :1962-1968
[6]   CONFORMATIONAL-ANALYSIS OF SPIRANES .3. MANIFESTATION OF CHIRALITY IN THE NMR-SPECTRA OF SPIROBISDIOXANES AT LOW-TEMPERATURES [J].
DODZIUK, H ;
SITKOWSKI, J ;
STEFANIAK, L ;
MURSAKULOV, IG ;
GASANOV, IG ;
KURBANOVA, VA .
STRUCTURAL CHEMISTRY, 1992, 3 (04) :269-276
[7]   C-13 MAGNETIC-RESONANCE - UPFIELD SHIFTS CAUSED BY NITROGEN, OXYGEN, AND FLUORINE-ATOMS LOCATED AT LAMBDA POSITION AND ANTI-PERIPLANAR TO NUCLEUS OBSERVED [J].
ELIEL, EL ;
BAILEY, WF ;
KOPP, LD ;
WILLER, RL ;
GRANT, DM ;
BERTRAND, R ;
CHRISTENSEN, KA ;
DALLING, DK ;
DUCH, MW ;
WENKERT, E ;
SCHELL, FM ;
COCHRAN, DW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (02) :322-330
[8]   CONFORMATIONAL ANALYSIS .8. VALIDITY OF NUCLEAR MAGNETIC RESONANCE METHOD OF ESTABLISHING CONFORMATIONAL EQUILIBRIA [J].
ELIEL, EL ;
MARTIN, RJL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (03) :682-&
[9]  
ELIEL EL, 1975, TETRAHEDRON, V49, P4339
[10]   BR3- VS BR2 - OPPOSITE DIASTEREOSELECTIVITY IN THE BROMINATION OF ENANTIOMERICALLY PURE KETALS [J].
GIORDANO, C ;
COPPI, L .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2765-2766