1969 Volume 42 Issue 12 Pages 3499-3504
2,3,4,5,6,6-Hexachloro-, 2,3,4,6,6-pentachloro-, and 2,4,6,6-tetrachloro-2,4-cyclohexadienones were found to undergo Diels-Alder reactions when the compounds were heated with such dienophiles as acrylic acid, methyl acrylate, methyl vinyl ketone, acrylonitrile, and ethyl vinyl ether. It was concluded, chiefly through analysis of these NMR spectra, that the reactions proceed stereospecifically to give a series of 7-substituted and polychlorinated bicyclo-[2.2.2] oct-5-en-2-ones, which is in agreement with the endo rule. The stereospecificity of these adducts does not, however, agree with the results of calculations by means of the perturbation method.
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