Photochemistry of diazonium salts. Syntheses of 2, 4-difluoroimidazole-5-carboxylic acid and related compounds

K Takahashi, KL Kirk, LA Cohen

Index: Takahashi, Kazuyuki; Kirk, Kenneth L.; Cohen, Louis A. Journal of Organic Chemistry, 1984 , vol. 49, # 11 p. 1951 - 1954

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Citation Number: 20

Abstract

Catalytic hydrogenolysis, effective for the synthesis of 2-aminoimidazoles from 2-(arylazo) imidazoles, cannot be used to prepare 2-amino-4fluoroimidazolee because the fluorine atom is lost simultaneously; formamidinesulfinic acid, however, achieves the required conversion in good yield. Ethyl 2, 4d~ uoroimidazole-5-carboxylate is obtained by photolysis of ethyl 2-diazonio-4-fluoroimidazole-5-carboxylate in fluoroboric acid. The ester is ...