期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 19, 页码 7274-7282出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo9012942
关键词
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资金
- Foundation for Education and European Culture
- University of Crete [ELKE K.A. 2750]
Photooxidation of pyrrole adducts 7-10 has been investigated in order to establish a general reaction pattern and mechanism for the formation of the resulting oxygenated products. The reactions were performed in several solvents utilizing both type I and type 11 sensitizers. In most cases, photooxidations gave complex mixture of products. Among these products, 5,5- or 6,5-bicyclic lactams (11, 15, and 19), maleimide 12 unsaturated gamma-lactams (16 and 20), 5-hydroxylactams (13,17,and 21), and 5-methoxylactams (14,18, and 22) were isolated and characterized. Photooxidation of 2,5-dimethyl-substituted pyrrole 10 in aprotic solvents unexpectedly afforded aldehyde 23 as the major product. Moreover, photooxidation of pyrrole adduct 10 in protic solvents exclusively gave the unprecedented solvent-trapped products 24-27. The formation of products 11-22 was rationalized by the intermediacy of a common endoperoxide intermediate, which could be formed by both type I and type II mechanisms. Compounds 23-27 were most probably formed via an electron-transfer mechanism.
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