Acid-catalyzed rearrangement of 2-substituted and 2,4-disubstituted 8H-3-oxaheptalen-8-ones to 1 -Acyl-6-hydroxyazulenes

Add time:08/13/2019    Source:sciencedirect.com

It was found that intrifluroacetic acid, 2-methyl 8H-3-oxaheptalen-8-one was transformed into 2-hydroxy-3-methyl-7H-benzocyclohepten-7-one and 1-formyl-6-hydoxy-2-methylazulene, whereas 2,4-dimethyl-8H-3-oxaheptalen-8-one was under the same conditions into 1-acetyl-2-methyl-6-hydroxyazulene. 2-Phenyl- and 2,4-diphenyl-8H-3-oxaheptalen-8-on undergo the same skeletal as those which corresponding mono- and dimethyl derivatives suffer from, respectively.

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