Reaction of the a-diazoketone derived from 7-carboxyphthalide with rhodium acetate results in an internal cyclization to give a six-ring carbonyl ylide which is subsequently converted to 7carbomethoxyphthalide.
Cyclic carbonyl ylide formation from the rhodium (II) acetate catalyzed reaction of 1-diazoalkanediones
β 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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β¦ 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
π SIMILAR VOLUMES
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.