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Cyclic carbonyl ylide formation from the rhodium (II) acetate catalyzed reaction of 1-diazoalkanediones

✍ Scribed by Albert Padwa; Richard L. Chinn; Susan F. Hornbuckle; Lin Zhi


Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
293 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis


Treatment of 1-diazoalkanediones with rhodium (II) acetate results in cyclization of the intermediate rhodium carbenoid to give a cyclic carbonyl ylide which readily undergoes bimolecular dipolar cycloaddition with various dipolarophiles. a-Diazoketones are valuable synthetic intermediates, with considerable utility in the


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In presence of the homogenous Rh/Cr/I catalyst system methyl formate can be isomerized to acetic acid under CO-pressure with high conversion rates and excellent selectivity. This catalyst system has never been applied before for this reaction.