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Title: | α,5-Didehydro-3-picoline Diradicals from Skipped Azaenediynes: Computational and Trapping Studies of an Aza-Myers−Saito Cyclization |
Authors: | Kumar, Dalip |
Keywords: | Chemistry Mixtures Isomerization Alcohols Allenes Cyclization |
Issue Date: | May-2004 |
Publisher: | ACS |
Abstract: | On the basis of density functional calculations, the isomerization of skipped azaenediynes (C-alkynyl-N-propargylimines) to azaenyne allenes and subsequent rapid aza-Myers−Saito cyclization to α,5-didehydro-3-picoline were predicted. We prepared the N-propargylimine of 1-phenyl-3-tri(isopropyl)silylprop-2-yn-1-one, which undergoes proto-desilylation and isomerization to an azaenyne allene when treated with tetrabutylammonium fluoride. In the presence of 1,4-cyclohexadiene, this azaenyne allene affords 6-phenyl-3-picoline and other products corresponding to the trapping of an α,5-didehydro-3-picoline diradical. |
URI: | https://pubs.acs.org/doi/10.1021/ol049266r http://dspace.bits-pilani.ac.in:8080/xmlui/handle/123456789/3084 |
Appears in Collections: | Department of Chemistry |
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