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The readily available α,α'-phthalimidoyldibromide 2 has been converted to the first reported N-substitutedoxyallyl cation by treatment with either CF 3 CH 2 OH or 3M LiClO4Et2O in the presence of Et 3 N. The formation of this reactive intermediate has been demonstrated by its in situ cycloaddition with cyclopentadiene and furan.