Liquid-assisted vortex grinding supports the single-step solid-state construction of a [2.2] paracyclophane

We employ vortex grinding to generate a [2.2] paracyclophane in the organic solid state. The vortex grinding is aided with the addition of a small amount of liquid phase to facilitate topochemical [2 + 2] photodimerizations that generate the cyclophane stereoselectively and in up to quantitative yield. The use of the liquid phase increases the scope of the vortex method.