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Quantum chemical calculations carried out at the DFT level of theory allowed the rationalization of the results observed in the cycloaddition of 1\u2010methyl\u20105\u2010(trifluoromethyl)azafulvenium methide and <jats:italic>N<\/jats:italic>\u2010substituted maleimides. The study revealed that for 1,7\u2010cycloadducts the major products are obtained in the <jats:italic>trans<\/jats:italic> configuration through the unusual <jats:italic>exo<\/jats:italic>\u2010cycloaddition mode, whereas for 1,3\u2010cycloadducts the <jats:italic>cis<\/jats:italic> counterparts are obtained from this unexpected approach. In addition, under flash vacuum pyrolysis or conventional thermolysis conditions 1\u2010methyl\u20105\u2010(trifluoromethyl)azafulvenium methide undergoes an allowed suprafacial sigmatropic [1,8]H shift leading to the formation of 2\u2010methyl\u20103\u2010(trifluoromethyl)\u20101\u2010vinyl\u20101<jats:italic>H<\/jats:italic>\u2010pyrrole.<\/jats:p>","DOI":"10.1002\/ejoc.201301922","type":"journal-article","created":{"date-parts":[[2014,4,3]],"date-time":"2014-04-03T07:55:44Z","timestamp":1396511744000},"page":"2933-2941","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["1\u2010Methyl\u20105\u2010(trifluoromethyl)azafulvenium Methide, an Intermediate That Undergoes Reaction through \u201cUnusual\u201d <i>cis<\/i>\u2010<i>exo<\/i>\u20101,3\u2010 and <i>trans<\/i>\u2010<i>exo<\/i>\u20101,7\u2010Cycloadditions"],"prefix":"10.1002","volume":"2014","author":[{"given":"Walter Jos\u00e9","family":"Pel\u00e1ez","sequence":"first","affiliation":[]},{"given":"Ana Julieta","family":"Pepino","sequence":"additional","affiliation":[]},{"given":"Gustavo Alejandro","family":"Arg\u00fcello","sequence":"additional","affiliation":[]},{"given":"Teresa M. 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