Synthesis of perfluorochemicals for use as blood substitutes,part II: electrochemical fluorination of partly fluorinated compounds |
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Authors: | Taizo Ono Yoshihisa Inoue Chikara Fukaya Yoshio Arakawa Youichiro Naito Kazumasa Yokoyama Kouichi Yamanouchi Yoshiro Kobayashi |
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Institution: | Central Research Laboratory, Green Cross Corporation, Chuo 1-1-47, Joto-ku Osaka 536 Japan;Tokyo College of Pharmacy, Horinouchi, Hachioji Tokyo 192-03 Japan |
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Abstract: | Electrochemical fluorination of 2-methoxy-1,1,1-trifluoro-2-(F-methyl) octane gave the corresponding perfluorinated ether in 27% yield, along with cyclic by-products in 9%. A mixture of partly fluorinated tertiary amines, consisting of 1-dipropylamino-F-1-propene and 1-dipropylamino-2-hydryl-F-propane, did not afford a superior yield of tri(F-propyl)amine compared to the unfluorinated tripropylamine. 1-Diethylamino-2-(F-methyl)-F-1-pentene was fluorinated to give the corresponding F-tertiary amine in fairly good yields, together with 1-di(F-ethyl)amino-2-hydryl-2-(F-methyl)-F-pentane and their fragmented products. The study indicates that blocking of the α-carbon atom of an ether with F-methyl groups seems to reduce fragmentation, resulting in good yields of an unrearranged product. However, partial fluorination of a tertiary amine prior to electrochemical fluorination rather allows high yields of undesired by-products, as far as our experiments were concerned. |
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