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Photochemische Reaktionen 100. Mitteilung . Photochemistry of N‐Acylimidazoles. V. Photolysis of the N‐Acylimidazoles of Dehydroabietic Acid and of 13‐Deisopropyl‐10‐epi‐dehydroabietic Acid
Author(s) -
Iwasaki Shigeo
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610811
Subject(s) - chemistry , photodissociation , moiety , imidazole , fragmentation (computing) , hydrogen atom abstraction , medicinal chemistry , stereochemistry , hydrogen , photochemistry , organic chemistry , computer science , operating system
The irradiation of 1‐(dehydroabietoyl) imidazole (3) gave no Type II elimination product but yielded instead compounds 6 and 7 by migration of the imidazolylcarbonyl group from C(4′) to C(6′) of the abietan moiety, probably via a cyclobutanol intermediate. Similarly, irradiation of 1‐(13′‐deisopropyl‐10′‐epi‐dehydro‐abietoyl)imidazole (13) gave only a small amount of Type II fragmentation product 20 , the main products derived from γ‐hydrogen abstraction being the cyclobutanol derivatives 16 and 17 .