1986 Volume 1986 Issue 5 Pages 681-686
The reactions of polyfluoroalkyl o-nitrobenzenesulfonates [1a-1d] with 1, 4-diazabicyclo[2. 2. 2]octane (DABCO) were investigated under the various conditions. The sulfonates ([1a] and [1b]) having shorter polyfluoroalkyl groups reacted with DABCO at 35°C in benzene to give 1-(polyfluoroalkyl)-4-aza-1-azoniabicyclo[2. 2. 2]octane o-nitrobenzenesulfonates ([2 a-I] and [2 b-I]) in high yields (93-94%). However, the reactions of the longer polyfluoroalkyl sulfonates ([1c] and [1d]) did not take place under the same conditions. At higher temperature (80°C), [1a-1d] gave 1-[2-[4-(polyfluoroalkyl)-1-piperadinyl]ethyl]-4-aza-1-azoniabicyclo[2. 2. 2]octane o-nitrobenzenesulfonates [3 a-I-3 d-I], without giving [2 a-I-2 d-I]. Aprotic solvents such as DMSO, DMF and sulfolane promoted the reaction of [1a] with DABCO even at room temperature (about 20°C), forming a mixture of [2 a-I]and [3 a-I].
The results of the reactions of ethyl p-toluenesulfonate and 2, 2, 2-trifluoroethyl iodide with DABCO were compared with those of [1a] with DABCO.
The quarternary ammonium cations and cluster ions were observed in secondary ion mass spectra (SIMS) analysis of the quarternary ammonium compounds prepared in these reactions and were useful for identification of these compounds.
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