Photosensitized (Electron-Transfer) Rearrangements of Cinnamyl Alcohol Derivatives

Article abstract of DOI:10.1021/jo00172a023

Specific electron-donor compounds are capable of photosensitizing the rearrangement and solvolysis of several cinnamyl alcohol derivatives.Under suitable conditions, the formation of rearranged α-phenylallyl derivatives occurs in synthetically useful yields.The intermediates in this process have ionic character and have been trapped by methanol as methyl ether derivatives.The ability of the photosensitizers to effect these electron-transfer-initiated reactions correlates well with the enthalpy of reaction calculated by the Weller equation.