Stereoselective chlorination of non-conjugated heterocyclic alkenes
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Abstract: |
Diels-Alder adducts of 4-substituted triazolinediones (4-Ph, 4-n-Pr) with cyclopellladienes have heen reacted with chlorine in carbon tetrachloride. When R = Ph only, cis-dichloride adduct is obtained in a stereos pecific manner. However, when R = n-Pr, two products, the cis-dichloride adduct and the rearrangement adduct are obtained in a stereoselective manner. The adducts of these triazolinediones with 1,3-cyclohexadiene have also been reacted with chlorine. When R = Ph, the trans-dichloride is formed with a high degree of stereoselectivity (98%). However, when R = n-Pr, two products, the trans-dichloride and the rearrangement adduct are obtained in 4:1 ratio. |