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Photochemical Behavior of Iodoheterocyclic Derivatives in the Presence of Electron-Poor Olefins (2000)

D'Auria, Maurizio ; Ferri, Rachele ; Poggi, Gabriella ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 1653-1659

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ISSN: 1434-193X

Keywords: Photochemistry ; Furans ; Thiophenes ; Radicals ; Electron-poor olefins ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: ---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.

Additional Material: 3 Tab.

Type of Medium: Electronic Resource

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