SET photochemistry of phthalimide anion and its reactivity with hydrogen donors

The investigation of the photochemistry of phthalimide anion has uncovered its exceptional reactivity with hydrogen donors such as alcohols, toluene, ethers and amines. Photoreactions can be conducted to high conversions and photoadducts are formed in high yield and with predictable regioselectivity...

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Bibliographic Details
Published in:Tetrahedron 2002-09, Vol.58 (36), p.7267-7274
Main Authors: Sánchez-Sánchez, Cristobal, Pérez-Inestrosa, Ezequiel, Garcı́a-Segura, Rafael, Suau, Rafael
Format: Article
Language:English
Subjects:
electron transfer
imides
isoindoles
photochemistry
radicals and radical reactions
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Summary:The investigation of the photochemistry of phthalimide anion has uncovered its exceptional reactivity with hydrogen donors such as alcohols, toluene, ethers and amines. Photoreactions can be conducted to high conversions and photoadducts are formed in high yield and with predictable regioselectivity. Exploratory studies have revealed that SET from the excited phthalimide anion to phthalimide is a thermodinamically favourable step that produces the electrophilic phthalimidyl radical and is the key step of the process. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00756-1