Evidence for ambiphilic behavior in (CO)5W=NPh. Conversion of carbonyl compounds to N-phenyl imines via metathesis

Article abstract of DOI:10.1021/ja00013a024

(CO)₅ W=NPh (5) has been generated in the presence of aldehydes, ketones, and thioketones and found to undergo metathesis with these substrates to yield N-phenyl imines. The participation of complex 5 as a nucleophile in these reactions and the previously reported reaction of 5 with PPh₃ confirm the ambiphilic nature of (CO)₅W=NPh. This is consistent with the electronic structure of the model compound (CO)₅W=NMe, as obtained from extended Hückel calculations. The heteroatom-substituted nitrene complex (CO)₅W=NNMe₂ (7) is less electrophilic but still functions as a nucleophile in its reaction with PhCHO to give Me₂NN=CHPh.