Contrasting behaviour of TCNE and TCNQ zwitterionic benzoquinonemonoimine derivatives and coordination of a tricyanoethenyl substituent to Pd(0)

Abstract

The reaction of TCNE and TCNQ zwitterionic benzoquinonemonoimine derivatives under basic conditions resulted in HCN elimination to give a tricyanoethenyl derivative – which forms a π-complex with Pd(0) – or a stable malodinitrile salt, respectively. In the latter case, chemoselective C-alkylation was observed whereas oxidation led to dimerization by C–C coupling.