Tetrahedron letters

Synthesis, Fe (II)-induced degradation, and antimalarial activities of 1, 5-diaryl-6, 7-dioxabicyclo [3.2. 2] nonanes: direct evidence for nucleophilic O-1, 2-aryl shifts

M Kamata, M Ohta, K Komatsu, HS Kim, Y Wataya

Index: Kamata, Masaki; Ohta, Motoko; Komatsu, Ken-Ichi; Kim, Hye-Sook; Wataya, Yusuke Tetrahedron Letters, 2002 , vol. 43, # 11 p. 2063 - 2067

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Citation Number: 11

Abstract

1, 5-Diaryl-6, 7-dioxabicyclo [3.2. 2] nonanes 1a–d (1a: Ar= p-FC6H4, 1b: Ar= Ph, 1c: Ar= p- MeC6H4, 1d: Ar= p-MeOC6H4) were prepared by a modified method of photo-electron transfer oxygenation, and the reactions of 1 with FeBr2 were investigated under various conditions. The Fe (II)-induced degradation of 1 afforded various rearrangement products and fragmentation products through competitive single electron transfer (SET) and Lewis ...