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Controlled-potential reduction of cyclopropyl ketones

โœ Scribed by Mandell, Leon; Johnston, Judy C.; Day, R. A.


Book ID
125935716
Publisher
American Chemical Society
Year
1978
Tongue
English
Weight
314 KB
Volume
43
Category
Article
ISSN
0022-3263

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## Functionalized cyclopropyl ketones have been found to undergo facile reductive cyclopropane ring opening with samarium (II) diiodide in the presence of a proton source. These reactions were exceedingly rapid, taking place in most cases at -78ยฐC under neutral conditions. An ester group substitut

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The synthesis of the cyclopropyl silyl ketones 1 4 is described. The trimethylsilyl ketone 1 was prepared from geraniol ((E)-5) in ca. 10% overall yield by cyclopropanation leading to 6 , Cr03 oxidation to the aldehyde 8, reaction of the latter with trimethylsilyl anion to 14A + B, and CrO? oxidatio