17509-79-4Relevant articles and documents
Reaction of Guaiazulene with Bromine in Hexane and in Aqueous Tetrahydrofuran
Nozoe, Tetsuo,Shindo, Kimio,Wakabayashi, Hidetsugu,Kurihara, Teruo,Uzawa, Jun
, p. 687 - 688 (1995)
2-Bromoguaiazulenium bromide and 3,3-dibromo guaiazulenium bromide were obtained respectively from the reaction of guaiazulene and its 3-bromo compound with 1 equivalent of bromine in hexane at -20 deg C.The former compound afforded in methanol a mixture of guaiazulene, 3,3'-biguaiazulene, and oligomers, and gave 3-bromoguiazulene quantitatively with alkali.Dibromoguiazulenium bromide afforded with further moles of bromine in aqueous THF a mixture of guaiazulenequinone, 3-bromo-1-hydroxyquaiazulen-5-one, and a dark blue solid A in different ratios depending on the reaction conditions.
UNUSUAL REACTIONS OF GUAIAZULENE WITH N-BROMOSUCCINIMIDE AND SYNTHESIS OF VARIOUSLY FUNCTIONALIZED AZULENES USING THESE REACTIONS
Nozoe, Tetsuo,Shindo, Kimio,Wakabayashi, Hidetsugu,Kurihara, Teruo,Ishikawa, Sumio
, p. 991 - 1010 (2007/10/02)
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.
Autoxidation of Guaiazulene and 4,6,8-Trimethylazulene in Polar Aprotic Solvent: Structural Proof for Products
Matsubara, Yoshiharu,Takekuma, Shin-ichi,Yokoi, Katsumi,Yamamoto, Hiroshi,Nozoe, Tetsuo
, p. 1415 - 1428 (2007/10/02)
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.