Bulletin of the Chemical Society of Japan p. 1415 - 1428 (1987)
Update date:2022-08-05
Topics:
Matsubara, Yoshiharu
Takekuma, Shin-ichi
Yokoi, Katsumi
Yamamoto, Hiroshi
Nozoe, Tetsuo
Autoxidation of guaiazulene and 4,5,8-trimethylazulene at 100 - 120 deg 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-azulenequionone, 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.
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