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Photochemistry of 1, 2-diketones: 1,2-cyclodecanedione and 2, 3-pentanedione

โœ Scribed by W.H. Urry; D.J. Trecker; D.A. Winey


Publisher
Elsevier Science
Year
1962
Tongue
French
Weight
315 KB
Volume
3
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


As with the symmetrical, acyclic vicinal-diones previously investigated', the photocyclizations of these substances give predominantly 2-hydroxycyclobutanones.

Further mechanism studies have shown that the triplet state gives this reaction since it is photosensitized by benzophenone, and that with 4358 A0 light quantum yields of this reaction with 2,7-dimethyl-4, S-octanedione may be higher than unity.

With 1, 2-cyclodecanedione, an excellent yield (74%) is obtained of a substance


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1,2-Cyclodeeanedione (1) undergoes a novel photore.axrangement in the crystalline state that is different from the Norrish/Yang type II photocycl~!ion process observed in solution. A possible mechanism is presented arid discussed. @ 1997 Elsevier Science Ltd. Medium sized ring and macrocyelic diket