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Stereoelectronic control of facial selectivity in the Diels-Alder cycloaddition of sterically unbiased 5,5-diarylcyclopentadienes

✍ Scribed by Halterman, Ronald L.; McCarthy, Bridget A.; McEvoy, Marjorie A.


Book ID
120871487
Publisher
American Chemical Society
Year
1992
Tongue
English
Weight
714 KB
Volume
57
Category
Article
ISSN
0022-3263

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p-Facial selectivity in Diels-Alder reactions of cyclopentadienes having C( O)YR substituents at the 5-positions was predicted on the basis of the orbital mixing rule and was substantiated experimentally. The selectivity was disclosed to be highly dependent on the relative orbital energy between p H