Studies on the isomerization of substituted allyl alcohols over Raney nickel

Substituted allyl alcohols, namely crotyl alcohol, 4-methylpent-3-en-2-ol, cinnamyl alcohol, 4-phenylbut-3-en-2-ol, 1,3-diphenylprop-2-en-1-ol, cyclopent-2-en-1-ol, and cyclohex-2-en-1-ol were found to isomerize to the corresponding carbonyl compounds in the presence of Raney nickel. The mechanism appears to involve the "half-hydrogenated state" followed by reversal as in the case of the well-known isomerization of olefins during hydrogenation. Tricyclo-[5.2.1.02,6]-dec-3-en-4-ols were also found to undergo isomerization to tricyclo-[5.2.1.02,6]-decan-3-one. © 1984.