Abstract An exploration of the role of para-substituents on the balance between stability and reactivity of N-phenyl trifluoroacetimidates prompted the discovery of new reagents for the addition of allyl and benzyl protecting groups, namely O-allyl and O-benzyl N-(p-nitrophenyl) trifluoroimidates. These compounds are stable and crystalline at ambient temperature, making them ideal alternatives to existing benzylating and allylating reagents used under ...