Photochemical Behavior of Iodoheterocyclic Derivatives in the Presence of Electron-Poor Olefins

Abstract

Photochemical reactions of some haloheterocycles bearing electron‐withdrawing groups 1a‐d with electron‐poor olefins 2a‐c gave the addition products 3a‐f and 3h‐m in good yields. Other products obtained were the corresponding olefins 4a‐k and the alkanes 3g. These reactions involve homolytic cleavage of the carbon‐halogen bond to give the corresponding radical. The nature of these radicals has been studied. Ab initio calculations at the MP2/6‐31G* level are supportive of the formation of σ radicals. These radicals are electrophilic and interact with the HOMOs of the electron‐poor olefins.