Experimental study reveals diverse cycloaddition pathways for 1-phosphafulvenes, indicating strong chemical behavior analogies between phosphorus-carbon and carbon-carbon double bonds.
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.
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Hu et al. (2017) studied this question.
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