Photodecarbonylation of Ketodiacids as Ammonium Salts: Efficient Formation of C−C Bonds Between Adjacent Quaternary Centers in the Crystalline State
| Autor: | Farnosh Family, Miguel A. Garcia-Garibay |
|---|---|
| Rok vydání: | 2009 |
| Předmět: |
Carbon Monoxide
Organic Chemistry Inorganic chemistry Decarbonylation Disproportionation Pentanone Photochemical Processes Decarboxylation law.invention Homolysis Quaternary Ammonium Compounds chemistry.chemical_compound Crystallinity Differential scanning calorimetry chemistry law Pentanones Polymer chemistry Dicarboxylic Acids Ammonium Crystallization |
| Zdroj: | The Journal of Organic Chemistry. 74:2476-2480 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo802761t |
| Popis: | Here we report the crystallization and solid photochemistry of six quaternary ammonium salts of 2,4-di-p-carboxyphenyl-2,4-dimethyl pentanone. While salt formation resulted in solids with different melting temperatures and crystallinities, photochemical excitation in the solid state resulted in the chemoselective formation of a single product arising from the homolytic loss of CO followed by combination of the intermediate radical pair. Photochemical experiments in solution led to the product mixtures formed by combination and disproportionation of the corresponding free radical intermediates. The crystallinity of all salts was documented by DSC, 13C CP-MAS NMR, and XRPD. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|