PHOSPHONIC SYSTEMS .8. SOLUTION AND SOLID-STATE CONFORMATION OF DIASTEREOMERIC ADDUCTS OF DIETHYL PROP-2-ENYLPHOSPHONATE TO P-NITROBENZALDEHYDE

被引:13
作者
MULLER, EL [1 ]
ROOS, HM [1 ]
MODRO, TA [1 ]
机构
[1] UNIV PRETORIA,DEPT CHEM,PRETORIA 0002,SOUTH AFRICA
关键词
D O I
10.1002/poc.610060111
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mixture of diastereomeric adducts of lithiated diethyl prop-2-enylphosphonate to p-nitrobenzaldehyde was separated and the solution and the solid-state structures of the individual stereoisomers were studied. Conformational analysis demonstrated that in solution the most populated rotamer involves in both cases trans orientation of the PO3Et2 and O2NCH4 groups and a gauche relationship of the phosphoryl and hydroxyl groups. In the solid state the crystal structure determination demonstrated that the molecules exist in the same conformation as in solution, although the P = O...H-O hydrogen bonding changed from intramolecular to intermolecular (dimeric) interactions.
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页码:64 / 70
页数:7
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