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

Roberts, John D. and Sauer, Charles W. (1949) Small-Ring Compounds. III. Synthesis of Cyclobutanone, Cyclobutanol, Cyclobutene and Cyclobutane. Journal of the American Chemical Society, 71 (12). pp. 3925-3929. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151001-104317808

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Abstract

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%.


Item Type:Article
Related URLs:
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http://dx.doi.org/10.1021/ja01180a013DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01180a013PublisherArticle
Additional Information:© 1949 American Chemical Society. Received April 12, 1949. We are indebted to Dr. R. C. Lord, Jr., Mr. R. S. McDonald and Mr. E. Slowinski for the infrared determinations. [Charles W. Sauer] An abstract of a thesis submitted in partial fulfillment of the requirements for the Degree of Doctor of Philosophy.
Issue or Number:12
Record Number:CaltechAUTHORS:20151001-104317808
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151001-104317808
Official Citation:Small-Ring Compounds. III. Synthesis of Cyclobutanone, Cyclobutanol, Cyclobutene and Cyclobutane John D. Roberts and Charles W. Sauer Journal of the American Chemical Society 1949 71 (12), 3925-3929 DOI: 10.1021/ja01180a013
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60683
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:06 Oct 2015 16:33
Last Modified:03 Oct 2019 08:59

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