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 a nd the compounds of H(2)NCH(2)CXYZH (Z = O, NH; X = H, CH3; Y = H, CH3, C2H 5) type in the presence of triethylamine give 7-membered heterocycles with two and three heteroatoms. Reaction of ethylenediamine with perfluoro-2-met hylpent-2-ene results in 9-fluoro-5,9-bis(pentafluoroethyl)-6,8,8-tris(trif luoromethyl)-1, 4-diazabicyclo[5.2.0]nona-4,6-diene and with perfluoro-5-az anon-4-ene leads only to 2,4-bis(heptafluoro-propyl)-6,7-dibydro-1H[1.3.5]t hiazepine. Reaction of ethylene glycol with perfluoro-2-methylpent-2-ene re sults in 2-fluoro-2,4-bis-(heptafluoropropyl)-6,7-dihydro2H[1.5.3]dioxazepi ne. The routes of formation for these products have been discussed and the role of triethylamine in these reactions is elucidated. (C) 2001 Elsevier S cience B.V. All rights reserved.