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The bromination, chlorination, and nitration of 1,3-disubstituted 2-hydroxyazulenes were investigated. Bromination by bromine or NBS afforded 1-bromoazulan-2-one derivatives as kinetically-controlled products and 6-bromo-2-hydroxyazulene derivatives as thermodynamically-controlled products. Ghlorination by NCS gave 1-chloroazulan-2-one derivatives, while that by chlorine afforded further chlorine addition products. Nitration afforded a mixture of 1-nitroazulan-2-one and 6-nitro-2-hydroxyazulene derivatives. The ultraviolet, infrared, and NMR spectra of the products were discussed.
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Nozoe et al. (1974) studied this question.
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