The reaction of binucleophilic reagents containing 1,4-nucleophilic centers with perfluoro-2-methylpent-2-ene and perfluoro-5-azanon-4-ene

Reaction between perfluoro-2-methylpent-2-ene or perfluoro-5-azanon-4-ene and the compounds of H2NCH2CXYZH (Z=O, NH; X=H, CH3; Y=H, CH3, C2H5) type in the presence of triethylamine give 7-membered heterocycles with two and three heteroatoms. Reaction of ethylenediamine with perfluoro-2-methylpent-2-ene results in 9-fluoro-5,9-bis(pentafluoroethyl)-6,8,8-tris(trifluoromethyl)-1,4-diazabicyclo[5.2.0]nona-4,6-diene and with perfluoro-5-azanon-4-ene leads only to 2,4-bis(heptafluoro-propyl)-6,7-dihydro-1H[1.3.5]thiazepine. Reaction of ethylene glycol with perfluoro-2-methylpent-2-ene results in 2-fluoro-2,4-bis-(heptafluoropropyl)-6,7-dihydro-2H[1.5.3]dioxazepine. The routes of formation for these products have been discussed and the role of triethylamine in these reactions is elucidated.