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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 24, Number 7
BKCSDE 24(7)
July 20, 2003 

An Intramolecular Photosubstitution Reaction of N-(2,4-Dibromonaphthyl)-arenecarboxamide: Synthesis of 2-Arylnaphthoxazole
In-Soo Bae, Yoo-Shin Kim, Yong-Tae Park
Intramolecular photosubstitution, 2-Arylnaphthoxazole, N-(2,4-Dibromonaphthyl)benzamide, Charge-transferred excited singlet state, Photoreduction
Photoreactions of N-(2,4-dibromonaphthyl)arenecarboxamides in basic medium result in the intramolecular substituted products, 2-aryl-8-bromonaphthoxazoles in moderate yields and further photoreactions of the products afford the reduced products, 2-arylnaphthoxazoles. These reactions are straightforward for syntheses of naphthoxazole derivatives. Since the intramolecular photosubstitution of the bromoarenecarboxamide by the oxygen of its amide group is more effective than the photoreduction of the substituted product, 2-aryl-8- bromonaphthoxazole in basic medium, the intramolecular substituted product, 2-aryl-8-bromonaphthoxazole can be isolated. A charge-transfered excited singlet state of an imidol form of the 2-bromoarenecarboxamide is involved in the photosubstitution, whereas an excited triplet state of the 2-aryl-8-bromonaphthoxzole is closely involved in the photoreduction.
916 - 920
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