Allyl triflate, propargyl triflate, pentyl triflate, 2-(2-fluoro-2,2-dinitroethoxy)ethyl triflate, 2-fluoro-2,2-dmitroethyl triflate, and 1,2,3-propanetritriflate were prepared from the alcohols using triflic anhydride and pyridine. 1,4-Butaneditriflate was formed from tetrahydrofuran and triflic anhydride. In the presence of potassium carbonate, pentyl triflate, allyl triflate, propargyl triflate , 1,4-butaneditriflate, and 2-(2-fluoro-2-2 -dinitroethyoxy)ethyl triflate reacted in chlorinated hydrocarbon solvents at ambient temperature with 2-fluoro-2,2dinitroethanol to give the corresponding ethers, without skeletal rearrangement. 1,2,3-Propanetritriflate underwent monosubstitution and elimination to yield 3-(2-fluoro-2,2-dinitroethoxy)-2-propenyl triflate. Pentyl triflate and 2,2,2-trifluoroethanol gave pentyl 2,2,2-trifluoroethyl ether. When sodium sulfate was used instead of potassium carbonate to scavenge liberated triflic acid, pentyl triflate and 2,2-dinitropropanol gave a mixture of the 1-, 2-, and 3-pentyl ethers. Under these conditions, 2-fluoro-2,2-dinitroethanol, 2,2-dinitropropanol, and 2,2,2-trinitroethanol, as well as pentanol, reacted with isopropyl triflate to give the corresponding isopropyl ethers. Allyl triflate was allowed to react similarly with 2,2-dinitropropanol, 2,2,2-trinitroethanol, and 2,2-dinitro-l,3propanediol to give the allyl ethers.
