Please use this identifier to cite or link to this item: http://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: http://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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