Oxidation of isobutene and methylenecycloalkanes by palladium(II) acetate

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Reactions of isobutene, methylenecyclopentane, methylenecyclohexane and methylenecycloheptane with palladium acetate were studied in acetic acid at 30 to 80°. Two types of oxidation were identified: acetoxylation to allylic acetates (methylenecycloheptane) and oxidative coupling to dimers (isobutene and methylenecyclohexane). A mechanistic study indicated that the former was produced by thermal decomposition of the initially formed π-allylic complex. The latter process was presumed to proceed via an insertion of the olefin into the carbonpalladium bond in the acetoxypalladate adduct,{A figure is presented} followed by the elimination of the elements of acetic acid and palladium hydride. © 1974.




Kikukawa, K., Sakai, K., Asada, K., & Matsuda, T. (1974). Oxidation of isobutene and methylenecycloalkanes by palladium(II) acetate. Journal of Organometallic Chemistry, 77(1), 131–145. https://doi.org/10.1016/S0022-328X(00)89429-2

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