The photochemical dimerisation of resveratrol analogues in the solid state to generate chiral phenyl substituted cyclobutanes is described. NMR spectroscopic and X-ray crystallographic methods have confirmed that the dimerisation leads to the head to tail orientation of the phenyl group substituents in the cyclobutane derivative. Interestingly, the parent compound, resveratrol, in the solid state, did not form a cyclobutane dimer, but the O-acetyl analogues gave the corresponding cyclobutane dimers in high yield, suggesting that the close packing of molecules together with the electron density through the conjugated double bond of the resveratrol structure are important determinants for photodimerisation to occur in the solid state.

描述了固态白藜芦醇类似物的光化学二聚以产生手性苯基取代的环丁烷。NMR光谱和X射线晶体学方法已经证实，二聚化导致环丁烷衍生物中苯基取代基的头尾方向。有趣的是，固态的母体白藜芦醇没有形成环丁烷二聚体，但是O-乙酰基类似物以高收率给出了相应的环丁烷二聚体，表明分子通过共轭体紧密堆积在一起并具有电子密度白藜芦醇结构的双键是固态发生光二聚化的重要决定因素。