Allenyl azide cycloaddition chemistry: Exploration of the scope and mechanism of cyclopentennelated dihydropyrrole synthesis through azatrimethylenemethane intermediates

Ken S. Feldman, Malliga R. Iyer, Carlos Silva López, Olalla Nieto Faza

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

(Chemical Equation Presented) Detailed studies of the thermal conversion of 1-azidohepta-3,4,6-trienes into cyclopentennelated dihydropyrroles are presented. High levels of diastereoselectivity and regioselectivity are documented. A mechanistic proposal that accounts for all of the diverse results is developed through the use of density functional calculations. These calculations provide support for the intervention of unexpected mechanistic subtleties, such as the planarity of an azatrimethylenemethane diyl intermediate and an apparent Woodward-Hoffmann-type electrocyclization of a five-atom diyl array.

Original languageEnglish (US)
Pages (from-to)5090-5099
Number of pages10
JournalJournal of Organic Chemistry
Volume73
Issue number13
DOIs
StatePublished - Jul 4 2008

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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