FLUORINATION OF 2-ALKYL-SUBSTITUTED OXIRANES. THE SYNTHESIS AND PURIFICATION OF PERFLUORO(2-ALKYL-SUBSTITUTED OXANE)S

Article abstract of DOI:10.1016/S0022-1139(00)81770-4

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.