Generation and Trapping of a 1‑Phosphafulvene: An Illustration of the PC/CC Analogy

1-Phosphafulvenes
can be easily generated by dissociation of dimers
resulting from the reaction of phospholes with aldimines. As electron-rich
partners, they act as 4π phosphadienic systems toward alkenes
and alkynes in [4 + 2] cycloaddition reactions. As electron-poor partners,
they act either as 2π systems toward conjugated dienes in [2
+ 4] cycloaddition reactions via their PC double bond or as
6π systems toward phosphadienes in [6 + 4] cycloaddition reactions.