Less is more? Probing the template amount required for solid-state olefin [2 + 2] photocycloaddition in a ball mill

Abstract

The first template-assisted olefin [2 + 2] photocycloaddition performed in a ball mill is reported. Using catalytic amounts of template resorcinol (as low as 10 mol%) enables rapid, quantitative and stereoselective dimerisation of trans-1,2-bis(4-pyridyl)ethene. In situ Raman monitoring of the photomechanochemical reactions reveals sigmoidal reaction profiles for olefin consumption, which were analyzed using the Finke–Watzky and JMAK kinetic models.