On the mechanism of the dienone-phenol rearrangement of A 2-methyl-1,4-dien-3-one

✍ Scribed by Paul J. Kropp

• Publisher: Elsevier Science
• Year: 1963
• Tongue: French
• Weight: 224 KB
• Volume: 4
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)90891-3

✦ Synopsis

IT ia well known that croae-conjugated cyclohexadienonee type I rearrange on treatment with aqueoue mineral acids cillcinnsti, Ohio of the general toamlrtureof two phenollc products, types III and VI. 1,2 Evidence has been presented that the formation of the tetrehydro-l-naphthol derivativea (type III) involves rearrangement through e q piro intermediate II (path A).3 mC formation of the tetrahydro-2-naphthol products (type VI) can be moat easily explained in terme of e simple 1,2-migration of the angular methyl eubetituent (path C). However, a second, albeit more complex, reaction pathway can be invoked to account for the formation of products of the type VI (path B): initial migretion of the methyl group to the alternate angular position, followed by further rearrangement of the resulting cation IV through a epiro intermediate V.