Unconventional catalytic allylation of 5-norbornene-2,3-dicarboxylic anhydrides: 7-oxa and 7-aza analogues

The catalytic allylation of 7-oxanorbornene, 7-azanorbornene, and bicyclo2.2.2]octenoic anhydride was performed for the first time. It was found that the structures of allylation products and ratios between them were analogous to those for corresponding carbocyclic derivatives. The presence of a substituent at the double bond of a substrate makes this reaction impossible. Comparative experiments were performed for evaluating the relative reactivity of double bonds in 7-oxanorbornene, 7-azanorbornene, and their carbocyclic analogs.