Bis(diethylamino)carbene and the mechanism of dimerisation for simple diaminocarbenes

Abstract

Bis(diethylamino)carbene is kinetically stable to dimerization in THF at ambient temperature; dimer formed during carbene generation arises from reaction of the carbene with the precursor formamidinium ion; this is probably the commonest route to tetraaminoethene dimers, and in a related case the intermediate protonated tetraaminoethene can be observed by NMR.