Bis(N-piperidyl)carbene and its slow dimerisation to tetrakis(N-piperidyl)ethene

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Roger W. Alder and Michael E. Blake


Abstract

An unhindered bis(sec-amino)carbene can be generated by deprotonation of an amidinium ion with lithium diisopropylamide, and undergoes remarkably slow dimerisation to the corresponding tetraaminoethene.


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