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 con
Carbonyl ylide formation in the reaction of methylene with acetone
โ Scribed by Nicholas J. Turro; Yuan Cha
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 130 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Photolysis of diazomethane in acetone yields a carbonyl ylide as an intermediate.
The reaction of carbene with nitriles' and ketones2 to form the corresponding ylides has received considerable attention. In nitrile solvent, methylene (CH2) has been found to react with the nitrile to form nitrile ylide, which is detectable by spectroscopy and product analysis.3
The formation of carbonyl ylide from methylene reaction with ketone has been proposed as an intermediate in the reaction with acetone 4 and formaldehyde, 5 respectively. We now report the results
๐ SIMILAR VOLUMES
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.
During the course of our investigation of the synthesis of oic-triasoles by reacting a-keto-and a-ester phosphorus ylides with acyl asides and ethyl asidoformate (1 + 2 + z), we found that the N-l substituted triasoles,isomerised to the N-2 substituted triasoles (1 + A) under the basic reaction cond