FILLED-ORBITAL REPULSION - A NEW FACTOR IN PI-FACIAL SELECTIVITY OF DIELS-ALDER REACTIONS

被引:30
作者
COXON, JM [1 ]
FONG, ST [1 ]
MCDONALD, DQ [1 ]
STEEL, PJ [1 ]
机构
[1] LINCOLN COLL,DEPT CHEM,CANTERBURY,NEW ZEALAND
关键词
D O I
10.1016/S0040-4039(00)60084-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dimethyl acetylenedicarboxylate and N-phenyl-1,2,4-triazolinedione add to ether 1 from the more sterically congested face of the diene syn to the cyclobutane ring. The interaction of the ether oxygen lone pair with the dienophile acetylenic pi-orbital or azo n-orbitals orthogonal to the forming sigma-bonds is important in determining the observed facial selection.
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页码:163 / 166
页数:4
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