EVIDENCE FOR AMBIPHILIC BEHAVIOR IN (CO)5W=NPH - CONVERSION OF CARBONYL-COMPOUNDS TO N-PHENYL IMINES VIA METATHESIS

(CO)5W = 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 Huckel 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.