Imidazolidine

Imidazolidine

Kinetics and Mechanism of the Inhibited Polymerization of Vinyl Monomers

Published in Richard A. Pethrick, Gennadi E. Zaikov, Teiji Tsuruta, Naoyuki Koide, Polymer Yearbook 13, 2019

M.D. Goldfein, G.P. Gladyshev, A.V. Trubnikov

Compared to the above nitroxyles based on imidazoline and imidazolidine have a number of advantages. The additional atom of nitrogen or of N-oxide group in combination with the functional group allows complexation and cyclic metallizing without the radical center being used. Existence of imines or imine-N-oxide groups gives a much higher stability in acid medium and is an important factor when they are used as inhibitors of polymerization of methyl acrylate. Imidazoline-N-oxides have the largest inhibiting activity as the agents terminating the oxidizing chains and traps for short-lived radicals.

Reactions of thiocarbonyl compounds with electrophilic and nucleophilic carbenes as well as with their metal complexes

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Journal Information

Published in Journal of Sulfur Chemistry, 2020

Grzegorz Mlostoń, Heinz Heimgartner

Reactions of DMC (115a) with aryl isothiocyanates occur in a different manner and deserve attention as they lead to new heterocyclic products. In these reactions, attack of the nucleophilic carbene onto the heterocumulene –N = C=S unit leads to the short-lived dipolar intermediate 146, which subsequently is efficiently trapped by another molecule of the starting aryl isothiocyanate yielding the five-membered imidazolidine-2,5-dithione 147 as the product of a regioselective [3 + 2]-cycloaddition [58] (Scheme 38).

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Kinetics and Mechanism of the Inhibited Polymerization of Vinyl Monomers

Reactions of thiocarbonyl compounds with electrophilic and nucleophilic carbenes as well as with their metal complexes