Allenyl azide cycloaddition chemistry: exploration of the scope and mechanism of cyclopentennelated dihydropyrrole synthesis through azatrimethylenemethane …

KS Feldman, MR Iyer, CS López…

Index: Feldman, Ken S.; Iyer, Malliga R.; Lopez, Carlos Silva; Faza, Olalla Nieto Journal of Organic Chemistry, 2008 , vol. 73, # 13 p. 5090 - 5099

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Citation Number: 19

Abstract

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 ...