REACTIVE E=C(P-P)PI SYSTEMS .22. TRIFLUOROMETHYLSELENOCARBONYLFLUORIDE - SYNTHESIS AND REACTIONS WITH 1,3-DIENES AND SECONDARY-AMINES

The red-violet trifluoromethylselenocarbonylfluoride SeC(F)CF3 (1) is produced quantitatively by thermal 1,2-elimination of Me3SnF from trimethylstannylpentafluoroethylselane Me3SnSeC2F5 (2) at 300°C and 10-2 torr. 1 is less inert than the related selenocarbonyldifluoride SeCF2 and shows a strong dienophilicity. The reactions of 1 with 2,3-dimethyl-1,3-butadiene, isoprene, cyclopentadiene, pentamethylcyclopentadiene and 1,3-cyclohexadiene, respectively, afford the corresponding Diels-Alder adducts 3-7 in high yields (70-98%). Compound 1 reacts with secondary amines, such as dimethyl-, diethyl- or di-isopropylamine and pyrrolidine to give trifluoromethyl selenocarbonylamides F3CC(Se)NR2 (8-11). All the new compounds of this study (2-11) have been characterized by elemental analysis (C, H, N) and spectroscopic investigations (MS, IR, NMR). © 1990.