In order to gain deep insight into the mechanism of the synthetically well established Rh(Ⅱ)-mediated intramolecular C-H insertion reaction, the classic physical organic chemistry method, the Hammett linear free energy correlation, has been applied. In the development of new synthetic methodologies of α-diazo carbonyl compounds, it was found that Cu(acac)2 can effectively promote the diazo decomposition and resulted in selective intramolecular N-H insertion. On the other hand, the Wolff rearrangement of the α-diazo carbonyl compounds catalyzed by Ag(Ⅰ) has been applied to the efficient synthesis of optically pure α-lactams.

Key words: CARBONYL COMPOUNDS, RUTHENIUM COMPLEX, COPPER COMPLEX, SILVER COMPLEX, LACTAM P, DIAZO COMPOUNDS, METAL COMPLEX, INSERTION REACTION, DECOMPOSITION REACTION, REACTION MECHANISM, SYNTHESIS