Synonyms:Disilene;15435-77-5;Q1530103
The study investigates the cycloaddition reactions of two stable disilenes, tetramesityldisilene (1) and trans-1,2-di-t-butyl-1,2-dimesityldisilene (3), with various 1-alkynes such as phenylacetylene, ethoxyacetylene, carbomethoxyacetylene, and trimethylsilylacetylene. These reactions, conducted in benzene solution at 80°C, produce air-stable disilacyclobutenes (2a-d and 4a-b). The products are isolated as colorless crystalline solids after recrystallization from hexane. The study finds that the cycloaddition of disilene 3 to alkynes yields equal amounts of both stereoisomers, suggesting a stepwise mechanism. Unlike previously reported disilacyclobutanes, the products 2a-d and 4a-b do not react with atmospheric oxygen due to steric protection from bulky groups on silicon. The study also notes that only polar alkynes react with disilene 1, hinting at a possible ionic mechanism involving a dipolar intermediate. Further research is needed to elucidate the exact mechanism of alkyne cycloaddition to stable disilenes.
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