Mechanism of Reductive Elimination of Acetophenone from N(CH3)4+-

Article abstract of DOI:10.1021/ja00528a034

Decomposition of N(CH3)4^+- (1) in the presence og P(C6H5)3 gives N(CH3)4⁺Mn(CO)4^- and provides evidence for a Mn(CO)4^- intermediate.Decomposition of 90percent 13C-acetyl labeled N(CH3)4^+- (1A) gave 42.7percent 13C-labeled acetophenone.Decomposition of 90percent 13C-benzoyl labeled N(CH3)4^+- (1b) gave 6.0percent 13C-labeled acetophenone.These results are interpreted in terms of a mechanism involving loss of CO from 1 and formation of a five-coordinate intermediate Mn(CO)3(COCH3)(COC6H5)^- (2), which is in rapid equilibrium with benzoylmethyl intermediate Mn(CO)4(CH3)(COC6H5)^- (3).Conversion of 3 to the acetylphenyl intermediate Mn(CO)4(C6H5)(COCH3)^- (4) is followed by reductive elimination to give acetophenone.