UNUSUAL STEREOSELECTIVITY IN THE DIELS-ALDER ADDITION OF CYCLOPENTADIENE WITH THE BICYCLO[2.2.2]OCTENE NUCLEUS

被引:16
作者
WILLIAMS, RV [1 ]
TODIME, MMR [1 ]
ENEMARK, P [1 ]
VANDERHELM, D [1 ]
RIZVI, SK [1 ]
机构
[1] UNIV OKLAHOMA,DEPT CHEM,NORMAN,OK 73019
关键词
D O I
10.1021/jo00076a039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclopentadiene adds to the substituted and electronically activated double bond of bicyclo[2.2.2]octa-2,5-diene-2,3-dicarboxylic anhydride with pronounced endo selectivity. Only two of the four possible stereoisomers were formed. The stereochemical course of the reaction was determined by X-ray crystallography and by a combination of chemical and spectroscopic techniques.
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页码:6740 / 6744
页数:5
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