Cycloaromatization of 1,4-pentadiynes: a viable possibility?
[structure: see text] The effects of several mostly sigma-withdrawing, pi-donating substituents X on the hitherto unknown Bergman-like cyclizations of 3-substituted 1,4-pentadiynes were studied at the BLYP/6-311+G//BLYP/6-31G level of theory. As the cyclization with X = OH(+) has the lowest barrier and is about thermoneutral, we predict that the title reaction is viable, for instance, through activation of derivatives with X = O with Lewis acids.
Kawatkar
Sameer P
SP
Department of Chemistry, University of Georgia, Athens, Georgia 30605-2556, USA.
Schreiner
Peter R
PR