Cyclohexenone derivatives. Part VII. Novel aromatisation reaction of some aryloxocyclohexenylacetic acid derivatives

Nasipuri, Dhanonjoy ; Roy Choudhury, Swadesh R. ; Bhattacharya, Amitava (1973) Cyclohexenone derivatives. Part VII. Novel aromatisation reaction of some aryloxocyclohexenylacetic acid derivatives Journal of the Chemical Society, Perkin Transactions 1 . pp. 1451-1456. ISSN 0300-922X

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Official URL: http://www.rsc.org/publishing/journals/P1/article....

Related URL: http://dx.doi.org/10.1039/P19730001451

Abstract

Methyl 2-aryl-6-oxocyclohex-1-enylacetates (I; R = Me) and some related compounds, when heated with a number of base-solvent systems, undergo aromatisation, the cyclohexenone system becoming phenolic with concomitant loss of the acetate side-chain. Sodium hydride in dimethylformamide at 100 ° is most effective for this transformation, and few alkoxides in aprotic solvents also catalyse the reaction. The mechanism is discussed. The results of dehydrogenation using pyridine hydrochloride are also reported.

Item Type:Article
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