N-(2,2-Dichloro-2-phenylethylidene)arenesulfonamides in reactions with secondary amines View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2008-07

AUTHORS

I. B. Rozentsveig, G. N. Rozentsveig, A. N. Mirskova, K. A. Chernyshev, L. B. Krivdin, G. G. Levkovskaya

ABSTRACT

N-(2,2-Dichloro-2-phenylethylidene)arenesulfonamides were synthesized by a modified procedure, and their reactions with secondary amines were studied for the first time. Reactions of imines with dialkylamines proceed at room temperature to afford α,α-dichloromethylbenzene and N,N-dialkyl-N′-(arenesulfonyl)formamidines arising from the haloform cleavage of the initially formed unstable N-(1-dialkylamino-2,2-dichloro-2-phenylethyl)arenesulfonamides. When the reaction is carried out upon cooling to 0°C, the products of the nucleophilic addition of secondary amines to azomethines, N-(1-dialkylamino-2,2-dichloro-2-phenylethyl) are formed in yields of no higher than 5%. Nonempirical calculations of 13C-1H spin-spin coupling constants and their experimental measurements for the series of the synthesized N-arenesulfonamides were performed to show that these compounds exist in solutions exclusively as E isomers. Preferable conformations of the investigated compounds and the relative energies of their E and Z isomers in the gas phase were determined by quantum-chemical calculations at the MP2/6-311G** level of theory. The NMR spectral data revealed restricted rotation of the N,N-dialkylamino group about the partially double C-NAlk2 bond in the molecules of N-arenesulfonylformamidines. More... »

PAGES

1371-1379

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070363208070141

DOI

http://dx.doi.org/10.1134/s1070363208070141

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1025247235


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