- UNUSUAL REACTIONS OF GUAIAZULENE WITH N-BROMOSUCCINIMIDE AND SYNTHESIS OF VARIOUSLY FUNCTIONALIZED AZULENES USING THESE REACTIONS
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Treatment of guaiazulene (Ia) with NBS in benzene gives various, side-chain-brominated compounds, but in hexane it affords exclusively 3-bromoguaiazulene (Id).Compound Id is stable in hexane at 5 deg C in the absence of oxygen, whereas in benzene it changes very rapidly to a mixture of similar compounds as those directly obtained from Ia and NBS in benzene.Possible pathways for the formation of these compounds are briefly discussed.By utilizing these reactions, various kinds of side-chain functionalized azulenes that are otherwise not available by conventional methods can be readily prepared from Ia.
- Nozoe, Tetsuo,Shindo, Kimio,Wakabayashi, Hidetsugu,Kurihara, Teruo,Ishikawa, Sumio
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p. 991 - 1010
(2007/10/02)
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- Facile Shifts of Bromine Atom on C-3 Position of Guaiazulene and Synthesis of Variously Functionalized Azulenes Using These Reactions
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Treatment of guaiazulene (1) with NBS in hexane gave exclusively 3-bromo compound, while in benzene it afforded various side-chain-brominated compounds.Shifts of bromine atom catalyzed by succinimide were observed in benzene, presumably via intermolecular radical pathways.Using these reactions, various side-chain-functionalyzed derivatives of 1, including epoxy compounds, were prepared.
- Nozoe, Tetsuo,Ishikawa, Sumio,Shindo, Kimio
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p. 353 - 356
(2007/10/02)
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- Autooxidation of Solid Guaiazulene and of the Solution in DMF in the Presence of Base or Acid: A Comparative Study of the Product Distribution
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Autooxidation of Guaiazulene was examined in detail under the following conditions: in a highly diluted DMF solution, in DMF in the presence of acid or base (at 80-100 deg C), and as solid state under sunlight or in the dark (at 25-50 deg C).In all cases a wide variety of products were obtained (33 separable compounds altogether), and a comparable study on the distribution of the products under the various reaction conditions was made to establish more precise reaction pathways for the formation of these interesting compounds.
- Takekuma, Shin-ichi,Marsubara, Yoshiharu,Yamamoto, Hiroshi,Nozoe, Tetsuo
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p. 475 - 482
(2007/10/02)
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