This contribution will outline some recent achievements made possible by replacing classically-used amino groups with more strongly p-donating ylidic substituents, with a particular focus on the iminophosphorano substituent (R3P=N-). By placing them in conjugation with an appropriate p-system, these substituents can lead to molecular properties that are not accessible with amino groups. As examples, it will be demonstrated that ylidic substituents (Y) impart increased nucleophilicity to pyridine, leading to some of the most active acylation catalysts, and that bis-2-pyridinylidenes featuring ylidic functionalities represent the most easily oxidized neutral organic compounds. These latter compounds have potential applications as homogeneous organic reducing agents.

Beyond amino groups: Pushing boundaries with ylidic p-donor substituents

247th National Meeting (2014)

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