Journal of Organic Chemistry p. 3967 - 3970 (1987)
Update date:2022-07-29
Topics:
Maruyama, Kazuhiro
Tamiaki, Hitoshi
In aqueous ammonia, silver(I)-catalyzed isomerization of quadricyclanes to norbornadienes was investigated.The catalytic action of silver(I) perchlorate induced rapid and clean isomerization of water-soluble quadricyclanes 1b-g to the corresponding norbornadienes 2b-g even at room temperature.In the isomerization, the silver(I) catalyst might attack 1 from the five-membered ring, which was different from the directions observed in the cobalt(II)-porphyryn- and rhodium(I)-catalyzed reactions.The present reactions proceed via the formation of the cationic species and the successive cleavage of the highly strained cyclopropane ring of 1 to give 2.
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