Journal of Organic Chemistry p. 602 - 606 (1986)
Update date:2022-08-11
Topics:
Maruyama, Kazuhiro
Tamiaki, Hitoshi
In an aqueous alkaline solution, the exothermic isomerisation of quadricyclane derivatives to norbornadiene derivatives catalyzed by cobalt-porphyrin complexes was investigated.By catalytic action of cobalt 5,10,15,20-tetrakis(p-carboxyphenyl)porphyrin (Co-TPPC), thermally stable and water-soluble quadricyclane derivatives 1a-l isomerised to the corresponding norbornadiene derivatives 2a-l quantitatively and suddenly even at room temperature in an aqueous sodium carbonate solution.It was seen that larger hydrophobicities of 1 enhanced the isomerization rate.The attacking direction of cobalt porphyrins toward quadricyclanes might be to the five-membered ring, which was different from that suggested in the action of Rh catalyst, i.e., attack to the three-membered ring.
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