Small-Ring Compounds. III. Synthesis of Cyclobutanone, Cyclobutanol, Cyclobutene and Cyclobutane

In the present work, methods for the preparation of cyclobutanone from methylenecyclobutane were investigated. Ozonization was not attempted because of the relative difficulty of adapting this procedure to large-scale laboratory operation. Satisfactory yields of cyclobutanone were obtained from methylenecyclobutane by oxidation to 1-(hydroxymethy1)-1-cyclobutanol and cleavage of the glycol with lead tetraacetate. Gustavson has previously obtained 1-(hydroxymethy1)-1-cyclobutanol in 40% yield by oxidation of methylenecyclobutane with dilute aqueous potassium permanganate. In the present investigation, 80-83% yields were achieved by performic acid oxidation using a modification of the procedure employed by Roebuck and Adkins for the preparation of trans-cyclohexandiol-1,2. A 39% yield was obtained in a single experiment using hydrogen peroxide in t-butyl alcohol. Oxidation of the glycol with lead tetraacetate in methylene chloride solution gave yields of cyclobutanone up to 90%. Periodate oxidation of the glycol was not successful. The over-all yield of cyclobutanone from pentaerythritol was 40%.