Synthesis of silicon-containing macrocyclic compounds by using intramolecular [2+2] photocycloaddition reactions of bis-dimethylsilyl-linked styrenes and stilbenes
| Autor: | Ko-ichi Nishimura, Ryu-ichiro Hiranabe, Hajime Maeda, Kazuhiko Mizuno |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Double bond Photoisomerization 010405 organic chemistry General Chemical Engineering General Physics and Astronomy General Chemistry Phenanthrene 010402 general chemistry 01 natural sciences Medicinal chemistry Cycloaddition 0104 chemical sciences Styrene chemistry.chemical_compound chemistry Intramolecular force Benzene Isomerization |
| Zdroj: | Journal of Photochemistry and Photobiology A: Chemistry. 364:472-477 |
| ISSN: | 1010-6030 |
| DOI: | 10.1016/j.jphotochem.2018.06.038 |
| Popis: | A method for the synthesis of silicon-containing macrocyclic compounds, using intramolecular [2 + 2] photocycloaddition reactions of bis-dimethylsilyl-linked styrene or stilbene derivatives, is described. Photoirradiation of benzene solutions of o- and m-bis(dimethylsilylmethyl)benzene derivatives, containing two styrene units, promotes efficient formation of intramolecular [2 + 2] photocycloadducts. In contrast, photoreaction of the corresponding para-substituted analog generates only dimers. Photoreactions of bis(dimethylsilylmethyl)benzene derivatives, possessing two stilbene units produce intramolecular [2 + 2] photocycloadducts along with products of cis-trans photoisomerization. The efficiencies of these intramolecular photoreactions depend on the distances between two double bonds undergoing [2 + 2] cycloaddition. Triplet-sensitized photoreactions of the stilbene derivatives lead to cis-trans isomerization exclusively. Finally, photoreactions of the stilbene derivatives in the presence of molecular oxygen produce phenanthrene derivatives as side products. |
| Databáze: | OpenAIRE |
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