ChemInform Abstract: 1,2-Substituted Acenaphthylenes. Part 14. Synthesis and Methoxydehalogenation of 5-Halogeno-1,2-acenaphthenedione Acetals.

✍ Scribed by V. F. ANIKIN; S. E. SAMBURSKII; A. V. MAZEPA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 35 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199832134

✦ Synopsis

Synthesis and Methoxydehalogenation of 5-Halogeno-1,2-acenaphthenedione Acetals.

-Since direct methoxylation of the 5-halogeno-1,2-acenaphthenediones (I) results in destruction of the α-diketone fragment, the acetal formation is attempted. Reaction of the diones (I) with 2,2-dimethylpropan-1,3-diol (II) affords a mixture of monoacetals (III) and (IV). While the acetal (IV) smoothly undergoes substitution of the halogen by the methoxy group, the acetal (III) does not afford methoxy dehalogenation products due to steric reasons. Acidic hydrolysis of the 5-methoxy acetal (VI) gives the hitherto unknown 5-methoxy-1,2-acenaphthenedione (VII). -(ANIKIN, V. F.; SAMBURSKII,