Collect. Czech. Chem. Commun. 1987, 52, 132-139

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

Vladimír Macháčeka, Vojeslav Štěrbaa and Antonín Lyčkab

a Department of Organic Chemistry, Institute of Chemical Technology, 532 10 Pardubice
b Research Institute of Organic Syntheses, 532 18 Pardubice-Rybitví


1H 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.