An interesting competition between 6π-electro- and Garratt–Braverman cyclization in bis-diene-allene sulfones: synergy between experiment and theory

Abstract

The reactivity of a series of bispropargyl sulfones with an ortho alkenyl moiety was studied. Under basic condition, these molecules isomerized to the bis-diene-allene system capable of undergoing 6π-electro-(EC) as well as Garratt–Braverman (GB) cyclization. The reaction generally favours the GB process but the balance can be tilted towards the 6π-EC pathway by suitable perturbation of structure and temperature. The findings are useful as the systems undergoing GB pathway can show DNA-damage activities.