Abstract
Equation presented. 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.
Original language | English |
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Pages (from-to) | 2059-2062 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 6 |
Issue number | 12 |
DOIs | |
State | Published - Jun 10 2004 |