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Cope rearrangement revisited

✍ Scribed by Hoffmann, Roald; Stohrer, Wolf D.

Book ID: 115443407
Publisher: American Chemical Society
Year: 1971
Tongue: English
Weight: 831 KB
Volume: 93
Category: Article
ISSN: 0002-7863
DOI: 10.1021/ja00754a042

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The observation of practically identical activation parameters for the Cope rearrangement 2 Ǟ 6 and its "frustrated" counterpart 1 Ǟ 5 indicates a two-step mechanism for the reaction 2 Ǟ 6. Direct proof of this interpretation comes from trapping experiments, which demonstrate the intermediate format

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In contrast to 2-aza and 3-aza-Cope rearrangements, 1 2 the 1-aza-Cope rearrangement is not common. One of the few examples of this reaction is the aza analog of the divinylcyclopropane