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Autoxidation of Guaiazulene and 4,6,8-Trimethylazulene in Polar Aprotic Solvent: Structural Proof for Products

1987; Oxford University Press; Volume: 60; Issue: 4 Linguagem: Inglês

10.1246/bcsj.60.1415

1348-0634

Yoshiharu MATSUBARA, Shin‐ichi Takekuma, Katsumi YOKOI, Hiroshi Yamamoto, Tetsuo Nozoe,

Photochemistry and Electron Transfer Studies

Abstract Autoxidation of guaiazulene and 4,6,8-trimethylazulene at 100–120°C in DMF (or HMPA) respectively yielded 25 and 17 separable products, including several known compounds. Most of these new compounds were derivatives of 1,5- and 1,7-azulenequinone, 1H-inden-1-one, naphthoquinone, and benzenoid, or dimeric and trimeric forms; structures of these products were established on the basis of spectroscopic (NMR, UV, IR, and MS) and half-wave potential (E1⁄2) data. 1H NMR (200-MHz) parameters of various azulene derivatives are given for comparative study. Possible reaction pathways are suggested for the formation of such a wide variety of interesting products.