STRUCTURE, CONFORMATION AND STEREOELECTRONICS OF 9,10-ANNELATED-1,4,5,8-TETRAOXADECALINS - A MULTIDISCIPLINARY PROBE

被引:7
作者
APED, P
FUCHS, B
GOLDBERG, I
SENDEROWITZ, H
SCHLEIFER, L
TARTAKOVSKY, E
ANTEUNIS, M
BORREMANS, FAM
机构
[1] TEL AVIV UNIV,RAYMOND & BEVERLY SACKLER FAC EXACT SCI,SCH CHEM,IL-69978 TEL AVIV,ISRAEL
[2] STATE UNIV GHENT,DEPT ORGAN CHEM,B-9000 GHENT,BELGIUM
关键词
D O I
10.1016/S0040-4020(01)86529-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The structure and conformation of the 9,10-annelated-1,4,5,8-tetraoxadecalins (3, 4 and 5) were investigated in solution using NMR spectroscopy, in the crystal using X-ray diffraction analysis and by computation, using the MM2 force field, suitably parameterized to include structural manifestations of the anomeric effect. The study focused on the geometry, viz., the structural parameters of the anomeric moieties and the ring conformation and degree of puckering, as affected by changes in the dihedral angle of the 9,10-annealing system. Very good agreement between the three methods was obtained, showing increased chair deformation, as the 9,10-substituents approach coplanarity.
引用
收藏
页码:5781 / 5796
页数:16
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