Abstract
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. 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. 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. 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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