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Syntheses of Some Bicyclo [3.3.0]octane Derivatives

Roberts, John D. and Gorham, William F. (1952) Syntheses of Some Bicyclo [3.3.0]octane Derivatives. Journal of the American Chemical Society, 74 (9). pp. 2278-2282. ISSN 0002-7863. doi:10.1021/ja01129a033.

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As part of a projected synthesis of pentalene (bicyclo [3.3.0]octatetraene), bicyclo [3.2.0]-2-hepten-6-one prepared by condensation of ketene and cyclopentadiene was converted by the Tiffeneau-Demjanov ring expansion procedure to a mixture of bicyclo [3.3.0]-2-octen-6-one and bicyclo [3.3.0]-2-octen-7-one. The ketonic mixture was reduced with lithium aluminum hydride and the resulting alcohols were converted to a mixture of tetrahydropentalenes by the Chugaev method. Unsuccessful attempts were made to transform the tetrahydropentalene mixture into pentalene by catalytic dehydrogenation procedures. Some of the steps in the Linstead synthesis of cis- and trans-bicyclo[3.3.O]octanes have been improved.

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Additional Information:© 1952 American Chemical Society. Received November 15, 1951.
Issue or Number:9
Record Number:CaltechAUTHORS:20151022-111327801
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Official Citation:Syntheses of Some Bicyclo [3.3.0]octane Derivatives John D. Roberts and William F. Gorham Journal of the American Chemical Society 1952 74 (9), 2278-2282 DOI: 10.1021/ja01129a033
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61413
Deposited By: Ruth Sustaita
Deposited On:22 Oct 2015 18:32
Last Modified:10 Nov 2021 22:48

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