Photochemical Behavior of Iodoheterocyclic Derivatives in the Presence of Electron-Poor Olefins
- Resource Type
- Authors
- Gabriella Poggi; Rocco Racioppi; Rachele Ferri; Giacomo Mauriello; Maurizio D'Auria
- Source
- European Journal of Organic Chemistry. 2000:1653-1659
- Subject
- Ab initio quantum chemistry methods
Chemistry
Radical
Organic Chemistry
Electrophile
Electron
Physical and Theoretical Chemistry
Photochemistry
Bond cleavage
- Language
- ISSN
- 1099-0690
1434-193X
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.