Cycloaromatization of 1,4-pentadiynes: a viable possibility?

Sameer P Kawatkar; Peter R Schreiner

doi:10.1021/ol0266424

Cycloaromatization of 1,4-pentadiynes: a viable possibility?

Org Lett. 2002 Oct 17;4(21):3643-6. doi: 10.1021/ol0266424.

Authors

Sameer P Kawatkar¹, Peter R Schreiner

Affiliation

¹ Department of Chemistry, University of Georgia, Athens, Georgia 30605-2556, USA.

PMID: 12375908
DOI: 10.1021/ol0266424

Abstract

[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.