A QTAIM and Electron Delocalization Computational Study of tert-Butylmethylene, Trimethylsilylmethylene, and Trimethylgermylmethylene. A New Method for Unambiguously Characterizing the Bonding between Pairs of Atoms in Reaction Intermediates

While studies on the experimental photolytic and thermolytic extrusion of nitrogen from tert-butyldiazomethane and tert-butyldiazirine and the decomposition of other precursors have shown a mixture of C-H and C-C insertion products depending on conditions, the analogous trimethylsilyldiazomethane undergoes solely Si-C insertion. Description of the singlet tert-butylmethylene intermediates potentially involved in the C-H and C-C insertion …