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

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 01期

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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