Journal of Organic Chemistry p. 5096 - 5099 (1982)
Update date:2022-08-04
Topics:
Munslow, William D.
Reusch, William
Pyrolysis of 3-isopropenyl-2-allylcyclohex-2-en-1-one (4) at ca. 275 deg C yielded 3,4,5,6-tetrahydro-5,5-dimethyl-1(2H)-naphthalenone (1) as the chief product.Higher pyrolysis temperatures also yielded methyl substituted α-tetralones derived from 1.Reductive methylation of 1 gave the trans-angularly methylated derivative 9 as the only product.The dienolate intermediate in this transforamtion was also trapped as a trimethyl ether, 8.Mechanisms for the pyrolytic rearrangement and the reductive alkylation are discussed.
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