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Reductive cleavage of cyclopropyl ketones

✍ Scribed by William S. Murphy; Sompong Wattanasin


Book ID
104243643
Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
157 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis


Aryl substituted cyclopropyl ketones are cleaved to acyclic ketones with zinc and zinc chloride or with zinc alone in refluxing alcohol.

Cyclopropanes are important synthetic intermediates due to their exceptional reactivity when functionalised', the cyclopropane 'trick", and their ready accessibility.' A number of methods have been used for the reductive cleavage of cyclopropyl ketones. Both zinc in


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Summatty: Reductive ring opening of the tetracyclic cyclopropyl ketones l\_ to 3 is described and affords selective entry to the tricyclo[4.4.01y605'g ldecane (sinularene) and to the tricyclo[5.4.01'7.06'10 lundecene (longifolene) skeletons. Controlled cleavage of cyclopropane intermediates provides