- Electrochemical fluorination of several esters derived from oxolane-2-yl-carboxylic acid, oxolane-2-yl-methanol and oxane-2-yl-methanol
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Electrochemical fluorination (ECF) of the ester derivatives of oxolane-2-yl-carboxylic acid (1), oxolane-2-yl-methanol (2) and oxane-2-yl-methanol (3) were investigated. Perfluoro(oxolane-2-yl- carbonylfluoride) (4) was obtained from derivatives of 1 and 2, and perfluoro(oxane-2-yl-carbonylfluoride) (5) was obtained from derivatives of 3 as the desired compounds, respectively. From the ECF of acetates of 2 and 3, perfluorospiroethers having a dioxolane ring were also obtained as the cyclization product in low yield together with the desired perfluoroacid fluoride (4 and 5). The structure of these perfluorospiroethers was confirmed by analyzing the chlorinated products, which were obtained by the reaction with AlCl3.
- Abe, Takashi,Tamura, Masanori,Sekiya, Akira
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p. 325 - 332
(2007/10/03)
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- FLUORINATION OF 2-ALKYL-SUBSTITUTED OXIRANES. THE SYNTHESIS AND PURIFICATION OF PERFLUORO(2-ALKYL-SUBSTITUTED OXANE)S
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Five kinds of 2-alkyl-substituted oxanes like 2-ethyloxane, 2-n-propyloxane, 2-iso-propyloxane, 2-n-butyloxane and 2-n-amyloxane were fluorinated electrochemically to give the corresponding perfluoro(2-alkyloxane)s.The perfluoro(2-alkyloxane)s were obtained in good yields from these starting materials together with isomeric perfluoro(2-alkyloxolane)s, perfluoro(2-alkyl-5-methyloxolane)s and perfluoro(dialkyl ether)s.The purification of the perfluoro(2-alkyloxane)s which contained small amounts of isomeric perfluoro(2-alkyloxolane)s was succesfully achieved by recovering the former unreacted after treating these mixtures with anhydrous aluminum chloride at 150-160 deg C during ca. 48 hrs in order to convert the latter into the easy-separable perfluoro-(2,5,5-trichloro-2-alkyloxolane)s.Small quantities of new perfluoro(5,5-dichloroalkanoyl chloride)s were also among the chlorination products.The spectroscopic data as well as the physical properties of these new fluorination products, and perfluoro(2,5,5-trichloro-2-alkyloxolane)s and perfluoro(5,5-dichloroalkanoyl chloride)s are presented.
- Abe, Takashi,Hayashi, Eiji,Baba, Hajime,Kodaira, Kazuo,Nagase, Shunji
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p. 353 - 380
(2007/10/02)
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