Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: VI. Reaction of 2-(cyclohex-2-en-1-yl)acetanilides with arylsulfanyl chlorides. Structural and quantum chemical ... View Full Text


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Article Info

DATE

2014-10

AUTHORS

N. M. Tsizorik, A. I. Vas’kevich, E. B. Rusanov, A. B. Rozhenko, M. V. Vovk

ABSTRACT

2-(Cyclohex-2-en-1-yl)acetanilides react with arylsulfanyl chlorides in chloroform to give 2-(2-arylsulfanyl-3-chlorocyclohexyl)acetanilides which undergo isomerization into 2-chloro-3-arylsulfanylsubstituted derivatives in polar solvents. According to the results of quantum chemical calculations, the addition of arylsulfanyl chlorides to 2-(cyclohex-2-en-1-yl)acetanilides is characterized by negative Gibbs energy. Specific conformation of the isomerization products is stabilized by weak (non-covalent) interactions which make them more energetically favorable than the initial compounds. The reactions of 2-(cyclohex-2-en-1-yl)acetanilides with arylsulfanyl chlorides in nitromethane in the presence of lithium perchlorate lead to the formation of mixtures of the corresponding addition products and electrophilic intramolecular cyclization products, N-[7-(arylsulfanyl)octahydro-1-benzofuran-2-ylidene]anilinium perchlorates, which are converted into free bases by treatment with sodium ethoxide. More... »

PAGES

1397-1408

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428014100029

DOI

http://dx.doi.org/10.1134/s1070428014100029

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1049692926


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