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The Mechanism of the Rearrangement of Fenchone

Lutz, Raymond P. and Roberts, John D. (1962) The Mechanism of the Rearrangement of Fenchone. Journal of the American Chemical Society, 84 (19). pp. 3715-3721. ISSN 0002-7863. doi:10.1021/ja00878a024.

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Fenchone labeled with ^(14)C in both methyl groups at the 3-position rearranges in concentrated sulfuric acid to 3,4-dimetliylacetophenone in which the radioactivity is essentially equally distributed between the methyl group adjacent to the carbonyl and the one in the ring 4-position (see Fig. 4). A by-product of the rearrangement is camphor, which is likewise in part converted to fenchone in sulfuric acid. The mechanisms of these conversions are discussed.

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Additional Information:© 1962 American Chemical Society. Received March 1, 1962. Supported in part by the Petroleum Research Fund of the American Chemical Society. Grateful acknowledgment is made herewith to the Donors of this Fund. United States Rubber Co. Foundation Fellow, 1960-1961.
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American Chemical Society Petroleum Research FundUNSPECIFIED
United States Rubber Co. Foundation FellowshipUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry2811
Issue or Number:19
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Official Citation:The Mechanism of the Rearrangement of Fenchone Raymond P. Lutz and John D. Roberts Journal of the American Chemical Society 1962 84 (19), 3715-3721 DOI: 10.1021/ja00878a024
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61297
Deposited By: Ruth Sustaita
Deposited On:20 Oct 2015 19:05
Last Modified:10 Nov 2021 22:46

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