A FACIALLY DISSYMMETRIC 1,3-CYCLOHEXADIENE AS A DIENOPHILE IN DIELS-ALDER REACTIONS WITH POLYHALOCYCLOPENTADIENES

被引：8

作者：

MARCHAND, AP ^{[1
]}

ZOPE, UR ^{[1
]}

BURRITT, A ^{[1
]}

BOTT, SG ^{[1
]}

机构：

[1] UNIV CANTERBURY,DEPT CHEM,CHRISTCHURCH 1,NEW ZEALAND

来源：

TETRAHEDRON | 1995年 / 51卷 / 34期

关键词：

DIELS-ALDER CYCLOADDITION; PI-FACIAL DIASTEREOSELECTIVITY; MO CALCULATIONS;

D O I：

10.1016/0040-4020(95)00519-E

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder cycloaddition of 1,2,3,4,5,5-hexachloro- and of 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene (2a and 2b, respectively) to hexacyclo[10.2.1.0(2,11).0(4,9).0(4,14).0(9,13)]pentadeca-5,7-diene-3,10-dione (1) occurs in each case with highly stereoselective attack of the diene upon that face of the dienophile which is anti to the carbonyl groups. The corresponding endo,anti adduct (i.e., 6 and 8, respectively) is obtained as the exclusive cycloadduct in each case. The structures of 6 and 8 were established unequivocally via X-ray crystallographic methods. The results of AM1 semi-empirical MO calculations for cycloaddition of 1 to 2a are in accord with experiment.

引用

页码：9319 / 9326

页数：8

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