Adduct of NacNacAl with Benzophenone and Its Coupling Chemistry.

Reaction of NacNacAl (NacNac=[DippNC(Me)CHC(Me)NDipp]- ) with one equivalent of benzophenone affords a ketylate species NacNacAl(η2 (C,O)-OCPh2 ) that undergoes easy cyclization reactions with unsaturated substrates. The scope of substrates included benzophenone, aldimine (PhNC(Ph)H), quinoline, phenyl nitrile, trimethylsilyl azide, and a saturated cyclic thiourea. The latter substrate reacted by an unusual C-N cleavage that left the C=S functionality intact. The new products were characterized by NMR spectroscopy and X-ray diffraction analysis.