Mechanism of the reaction of 1-methoxy- and 1-chloro-2,4,6-trinitrobenzene with dimethyl malonate anion

1 H NMR spectra have been used to prove the formation of 1,3- and 1,1-adducts in the reaction of 1-methoxy-2,4,6-trinitrobenzene with dimethyl malonate anion and formation of 1,3-adduct in the analogous reaction of 1-chloro-2,4,6-trinitrobenzene. Dimethyl 2,4,6-trinitrophenylmalonate is formed from 1-chloro-2,4,6-trinitrobenzene at the same rate and by the same mechanism as the 1,1-adduct from 1-methoxy-2,4,6-trinitrobenzene. The two reactions only differ in their rate-limiting steps.