Simons electrochemical fluorination of substituted homopiperazines(hexahydro-1,4-diazepines) and piperazines |
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Authors: | Takashi Abe Hajime Baba Masanori Tamura |
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Institution: | a Research Center for Fluorinated Greenhouse Gas Alternatives (F-Center), National Institute of Advanced Industrial Science and Technology (AIST), AIST Central 5, 1-1-1 Higashi, Tukuba, Ibaraki 305-8565, Japan b Department for New Refrigerants Research (c/o F-Center), Research Institute of Innovative Technology for the Earth (RITE), AIST Central 5, 1-1-1 Higashi, Tukuba, Ibaraki 305-8565, Japan c Institute for Structure and Engineering Material, National Institute of Advanced Industrial Science and Technology (AIST), Shimoshidami, Moriyama-ku, Nagoya 463-8560, Japan |
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Abstract: | Simons electrochemical fluorination (ECF) of 1,4-dimethyl-1,4-homopiperazine, methyl 4-ethylhomopiperazin-1-ylacetate and 1,4-bis(methoxycarbonylmethyl)-1,4-homopiperazine was studied. For comparison, ECF of three piperazines with a N-(methoxycarbonylmethyl) group(s) was also studied. ECF of 1,4-dimethyl-1,4-homopiperazine gave a low yield of corresponding perfluoro(1,4-dimethyl-1,4-homopiperazine) together with perfluoro(2,6-diaza-2,6-dimethylheptane) as the major product. Corresponding perfluoro(homopiperazines) with mono- and/or di-(fluorocarbonyldifluoromethyl) groups CF2C(O)F] at the 1- and/or 4-position were formed in low yields from methyl 4-ethylhomopiperazin-1-ylacetate and 1,4-bis(methoxycarbonylmethyl)-1,4-homopiperazine, respectively. These new seven-membered perfluoro(1,4-dialkyl-1,4-homopiperazines) were accompanied by the formation of mono- and/or di-basic linear perfluoroacid fluorides resulting from the CC bond scission at the 2- and 3-positions of the ring. From mono- and/or di-N-(methoxycarbonylmethyl)-substituted piperazines, corresponding perfluoropeperazines having the acid fluoride group(s) were formed in low yields. |
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Keywords: | Simons electrochemical fluorination Organofluorine compound 1-Alkyl-4-(methoxycarbonylalkyl)-1 4-homopiperazines Perfluoroacid fluorides Perfluoro(1 4-dialkyl-1 4-homopiperazines) Perfluoro(1 4-dialkyl-1 4-piperazines) |
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