1976 Volume 49 Issue 12 Pages 3558-3563
The Diels-Alder reactions of polychlorocyclopentadienes with substituted ethylenes were investigated, and the rates of the reaction and the endo : exo adduct distributions were determined. The introduction of a chlorine atom at the C5 position of cyclopentadiene resulted in an enhanced endo preference for substituents in the adducts, despite the depressed reactivity of the diene. This is contrary to what is to be expected from the so-called “selectivity-reactivity relationship in the Diels-Alder reaction.” The results in this work were explained in terms of steric interaction between the C5-chlorine atom of the diene and the substituent of dienophiles.
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