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Derivatives with carboxylate groups at C-4 and\/or C-5 act exclusively as 1,7-dipoles affording products resulting from the addition across the 1,7-positions. These 1,7-cycloadducts include chlorin and bacteriochlorin type macrocycles as well as steroidal analogues, compounds with relevance in medicinal chemistry. In contrast with this chemical behavior, 5-trifluoromethylazafulvenium methides can participate in both 1,7- and 1,3-dipolar cycloadditions. The generation and reactivity of benzodiazafulvenium methides is also discussed. <\/jats:p>\n               <jats:p>\n                  <jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"graphic\/j_pac-2016-0404_fig_002.jpg\" \/>\n               <\/jats:p>","DOI":"10.1515\/pac-2016-0404","type":"journal-article","created":{"date-parts":[[2016,6,23]],"date-time":"2016-06-23T20:06:47Z","timestamp":1466712407000},"page":"457-475","source":"Crossref","is-referenced-by-count":3,"title":["Chemistry of aza- and diazafulvenium methides in heterocyclic synthesis"],"prefix":"10.1515","volume":"88","author":[{"given":"Teresa M. V. D.","family":"Pinho e Melo","sequence":"first","affiliation":[{"name":"CQC and Department of Chemistry , University of Coimbra , 3004-535 Coimbra, Portugal"}]}],"member":"374","published-online":{"date-parts":[[2016,6,22]]},"reference":[{"key":"2024030513023972228_j_pac-2016-0404_ref_001","doi-asserted-by":"crossref","unstructured":"O. B. 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