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https://hdl.handle.net/10316/18065| Title: | Cycloaddition of trifluoromethyl azafulvenium methides: synthesis of new trifluoromethylpyrrole-annulated derivatives | Authors: | Nunes, Cláudio M. Silva, Manuela Ramos Beja, Ana Matos Fausto, Rui Melo, Teresa M. V. D. Pinho e |
Issue Date: | Jan-2010 | Publisher: | Elsevier | Serial title, monograph or event: | Tetrahedron Letters | Volume: | 51 | 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. Graphical abstract | URI: | https://hdl.handle.net/10316/18065 | DOI: | 10.1016/j.tetlet.2009.11.033 | Rights: | openAccess |
| Appears in Collections: | FCTUC Química - Artigos em Revistas Internacionais |
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| File | Description | Size | Format | |
|---|---|---|---|---|
| Tetrahedron Letters, 51 (2010) 411.pdf | 331.36 kB | Adobe PDF | View/Open |
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