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Solid State Photochemistry of Isocoumarins and Isothiocoumarins

✍ Scribed by Michael A. Kinder; Jürgen Kopf; Paul Margaretha

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
113 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐ1H-2-Benzothiopyran-1-ones (isothiocoumarins) and 1H-2-benzopyran-1-ones (isocoumarins) behave dissimilarly on solid state irradiation at room temperature as the former photocyclodimerize ef®ciently while the latter only undergo slow photodecomposition. Both 4H-naphtho[2,1-c]pyran-4-one and thiopyran-4-one turn out to be photostable under these same reaction conditions.

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Upon UV irradiation in the solid-state 4.4'-dimethylbenzophenone (la) underwent intermolecular hydrogen abstraction, followed by radical &pling, to give solely a dimeric product, 4-(2-hydroxy-2,2-di-p-tolyleth 1)-4'-methylbenzophenone (2). By contrast, 3.3'-dimethylbenzophenone (lb!. 3.4'-dimethylbe