Conclusions
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1.
The thermal acylation of azulene with diphenylacetic and malonic acids is structurally directed to the 1 and 3 positions. In 4,6,8-trimethylazulene the acylation is predominantly in the 2 position.
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2.
The thermal alkylation of 4,6,8-trimethylazulene with bromo(chloro) acetic acid leads to 4,6,8-trimethylazulenyl-1-acetic acid. The radical mechanism is postulated for the reaction.
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3.
The thermal reaction of the 1-acetyl-, 1-benzoyl-, and 1-phenylsulfonyl-4,6,8-tri-methylazulenes with monohaloacetic acids is accompanied by cleavage, and also by the partial 1–2 migration of the substituents. 1-Nitro- and 1-trifluoroacetyl-4,6,8-trimethylazulene do not react under similar conditions.
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4.
Ferrocene, pyrene, anthracene, 6,6-diphenylfulvene, and 2-phenylbenzo[b]cyclopenta-[e]pyran when heated with malonic acid give monoacetyl derivatives.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 235–238, January, 1979.
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Porshnev, Y.N., Erikhov, V.I., Cherkashin, M.I. et al. Thermal reactions of azulenes. with malonic, diphenylacetic, and haloacetic acids. Russ Chem Bull 28, 221–224 (1979). https://doi.org/10.1007/BF00925434
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DOI: https://doi.org/10.1007/BF00925434