SHORT COMMUNICATIONSAcrylamide and N-substituted acrylamides are used in both fine organic synthesis and industry as intermediate products for the preparation of carbo-and heterochain polymers and copolymers and polyfunctional acyclic and heterocyclic compounds. While performing our systematic studies on the synthetic potential of halogen-containing N-sulfonyl imines, which have become readily accessible as a result of development of methods for their synthesis from N,N-dichlorosulfonamides, polyhaloethenes, and phenylacetylene [1], we examined reactions of N-(2,2,2-trichloroethylidene)trifluoromethane-and -arenesulfonamides Ia-Ic and N-(2-phenyl-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide (Id) with acrylamides.We previously showed that carboxamides, ureas, and sulfonamides add to N-sulfonyl imines derived from polychlorinated aldehydes to give the corresponding symmetric and asymmetric 1,1-bis(acylamino)polychloroalkanes [1].In the present work we found for the first time that Schiff bases Ia-Id obtained from the corresponding N,N-dichloro sulfonamides, trichloroethylene, and phenylacetylene readily take up acrylamide (within 2-3 h) to give N-(1-sulfonylamino-2-polychloroethyl)-acrylamides IIa-IId. Heating of the reaction mixture to 40-50°C accelerates the process. We observed no formation of poly(acrylamide), though acrylamide is known to readily undergo polymerization in the presence of radical initiators.The structure of acrylamide derivatives IIa-IId was proved by spectral data and elemental analyses. The IR spectra of IIa-IId contained absorption bands due to stretching vibrations of the amide NH, carbonyl, and sulfonyl groups. Amides IIa-IId showed in the 1 H NMR spectra signals corresponding to protons in the aromatic rings, NH-CH-NH fragment, and vinyl group. The latter appeared as an ABX spin system. In the 13 C NMR spectra of IIa-IId we observed signals from carbon atoms in the polyhaloethyl fragment and carbonyl group; the CF 3 signal in the spectrum of IIa was split into a quartet due to coupling with fluorine nuclei.Compounds IIa-IId are colorless crystalline substances which are insoluble in water, poorly soluble in nonpolar organic solvents, and readily soluble in acetone, DMSO, and aqueous alkali. The presence of proton-donor and proton-acceptor substituents, polyhalomethyl fragments, and a double bond in molecules IIa-IId makes these compounds potential ligands for complex formation with metals and promising intermediate products for fine organic synthesis, specifically for the preparation of nitrogen-containing acyclic and heterocyclic compounds and carbo-and heterochain polymers and copolymers having labile hydrogen atoms. Structural features of amides IIa-IId could give rise to formation of strong intra-and intermolecular hydrogen bonds; therefore, these compounds may X = Cl, R = CF 3 (a), Ph (b), 4-ClC 6 H 4 (c); X = Ph, R = 4-ClC 6 H 4 (d). RSO 2 NH CH HN CCl 2 X C HC O CH 2
