Cycloaddition of trifluoromethyl azafulvenium methides: synthesis of new trifluoromethylpyrrole-annulated derivatives |
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Authors: | Cláudio M Nunes Ana Matos Beja Teresa MVD Pinho e Melo |
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Institution: | a Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal b Department of Physics, University of Coimbra, 3004-516 Coimbra, Portugal |
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Abstract: | The chemistry of trifluoromethyl azafulvenium methides was explored leading to a new route to trifluoromethylpyrrole-annulated systems. The first evidence of azafulvenium methides acting as 1,3-dipoles is reported. These azafulvenium methides showed site selectivity in the reaction with strong electron-deficient dipolarophiles leading exclusively to 1,3-cycloadducts. In the cycloaddition with less-activated dipolarophiles 1,7-cycloadducts resulting from 8π+2π] cycloaddition are also formed. FMO analysis of the cycloaddition reactions allowed the rationalization of the observed selectivity. |
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Keywords: | Trifluoromethylpyrroles 1 3-Dipoles 1 7-Dipoles Azafulvenium methides Azomethine ylides [8π+2π] Cycloaddition 1 3-Dipolar cycloaddition 1 7-Electrocyclization Microwave |
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