Abstract
N-Phenyl-N-triflylpropiolamides react with iodine chloride or iodine bromide by an intramolecular electrophilic ipso-halocyclization/nucleophilic halide addition sequence to furnish cyclohexadiene-spiro-γ-lactams. These products can undergo cleavage of the amide bond with primary amines and of the N–Cspiro bond with secondary amines, leading to N-alkyl-2-iodo-3-phenylacrylamides and N-(4-halophenyl)-2-iodo-3-(2-triflylamino)phenylacrylamides, respectively.
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