Photoinduced 6π‐electrocyclization of 2, 5‐dichlorothiophene containing benzofuranylacrylonitriles as efficient method for the generation of hydrogen chloride. (1st October 2022)

• Record Type: Journal Article
• Authors: Karibov, Turan T.; Lichitsky, Boris V.; Komogortsev, Andrey N.; Melekhina, Valeriya G.
• Is Part Of: Journal of heterocyclic chemistry. Volume 60:Number 2(2023)
• Page Start: 264
• Page End: 276
• Publication Date: 2022-10-01
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.4578
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract: The photochemical 6π‐electrocyclization of 1, 3, 5‐hexatriene system containing benzofuran and 2, 5‐dichlorothiophene fragments was investigated. It was shown that considered photoreaction regiospecifically leads to the formation of substituted benzo[ b ]thieno[2, 3‐ g ]benzofurans. Along with the formation of polyheterocyclic products the studied process is accompanied by the elimination of hydrogen chloride molecule. Based on the suggested transformation an efficient method for the photogeneration of strong acid was implemented. As a result, the starting thienyl substituted benzofurans can be used as photoacid generators (PAGs). The structure of one of the final products was established by X‐ray diffraction. Abstract : The photochemical 6π‐electrocyclization of a 1, 3, 5‐hexatriene system containing benzofuran and 2, 5‐dichlorothiophene fragments has been studied. It is shown that the considered photoreaction regiospecifically leads to the formation of substituted benzo[b]thieno[2, 3‐g]benzofurans and is accompanied by the elimination of a hydrogen chloride molecule.