Study on the reactivity of oxabicyclic alkenes in ruthenium-catalyzed [2+2] cycloadditions |
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Authors: | Burton Ryan R Tam William |
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Institution: | Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, Canada. |
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Abstract: | The ruthenium-catalyzed 2+2] cycloadditions of various bicyclic alkenes with an alkyne have been investigated. The presence of the oxygen in the bridgehead of the bicyclic alkene significantly enhanced the rate of the ruthenium-catalyzed 2+2] cycloadditions. The presence of a C1-substituent on the oxanorbornadiene decreased the rate of the cycloaddition and electron-withdrawing C1-substituents were found to be more reactive than electron-donating C1-substituents in the Ru-catalyzed 2+2] cycloaddition. The nature of the substituent on the benzene ring of oxabenzonorbornadienes showed little effect on the rate of the cycloaddition. |
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