Chemiluminescent and Non-Chemiluminescent Ozonations of Selected Electron-Rich Alkynes in Halomethanes
| Autor: | Horst P. Beck, Frank Werner, Kurt Schank |
|---|---|
| Rok vydání: | 2000 |
| Předmět: |
chemistry.chemical_classification
Organic Chemistry Alkyne Alkylation Photochemistry Cleavage (embryo) Biochemistry Medicinal chemistry Catalysis law.invention Inorganic Chemistry chemistry.chemical_compound Acetylene chemistry Nucleophile law Drug Discovery Electrophile Physical and Theoretical Chemistry Vicinal Chemiluminescence |
| Zdroj: | Helvetica Chimica Acta. 83:1611-1624 |
| ISSN: | 1522-2675 0018-019X |
| Popis: | Alkynes of sufficiently high nucleophilicity react with electrophilic O3 under conversion of the alkyne function to a vicinal dicarbonyl function. Contrary to earlier investigations with alkylated or arylated acetylene, products of complete C−C cleavage were not found as primary products, and, beyond that, peroxidic reaction products were absent. Trimethylsilylated alkynes reacted with O3 either by uptake of two or three O-atoms, but again without C−C cleavage or formation of peroxides. Two particularly electron-rich, symmetrically substituted alkynes revealed strong chemiluminescence during ozonation at low temperature, whereas this behavior was not observed with unsymmetrically substituted alkynes. The results are summarized in terms of a mechanistic discussion. |
| Databáze: | OpenAIRE |
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