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200517.fm Page 48 Friday, March 18, 2005 2:52 PM
2005
Oxidation
O 0212
17- 046
A Practical and User-Friendly Method for the Selenium-Free One-Step Preparation of 1,2-Diketones and Their Monoxime Analogues. — Oxidation of α-methylene ketones proceeds smoothly in the presence of NaNO2 in strongly acidic medium.
The reaction affords the diketone monoximes like (II) in the presence of equimolar
amounts of NaNO2, while the corresponding diketones like (III) are achieved with three
equivalents of NaNO2. The use of selenium reagents is completely avoided. A wide
range of α-methylene ketones is applicable, including cyclic, acyclic and aromatic
ketones as well as a monoterpenoid (XII). — (RUEEDI*, G.; OBERLI, M. A.;
NAGEL, M.; WEYMUTH, C.; HANSEN, H.-J.; Synlett 2004, 13, 2315-2318;
Org.-Chem. Inst., Univ. Zuerich, CH-8057 Zuerich, Switz.; Eng.) — Mischke
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