Transition metal-catalyzed pentannulation of propargyl acetates via styrylcarbene intermediates |
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Authors: | Yusuke Nakanishi |
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Institution: | Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan |
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Abstract: | The indene formation from phenyl-substituted sec- and tert-propargyl esters (terminal alkynes) was achieved by platinum or ruthenium catalysis via E-vinylcarbenoid intermediate. Considering the competitive reactions of pentannulation versus cyclopropanation, the equilibrium ratios of E and Z vinylcarbenoid intermediates from sec- and tert-propargyl esters are estimated at ca. 10:90 and 40:60, respectively. Two reaction pathways, Nazarov-type cyclization and/or metallacycle from styrylcarbenoid species, are proposed by considering ratios of products in the control experiment. |
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