| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5281620 | Tetrahedron Letters | 2010 | 4 Pages |
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 [8Ï+2Ï] cycloaddition are also formed. FMO analysis of the cycloaddition reactions allowed the rationalization of the observed selectivity.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Cláudio M. Nunes, Manuela Ramos Silva, Ana Matos Beja, Rui Fausto, Teresa M.V.D. Pinho e Melo,