Effective Synthesis of Hard-To-Reach 3,4-Disubstituted Thiophene Derivatives Based on bis(2-chloropropenyl) Sulfide

Abstract

An efficient approach for the synthesis of hard-to-reach 3,4-disubstituted thiophene derivatives: 4,5,9,10-tetrahydrothieno[3',4;5,6]-cycloocta[1,2-c]thiophene, 1H,4H-thieno[3,4-d][1,2]dioxine, 4-(hydroxymethyl)thiophene-3-carbaldehyde, based on consecutive transformations of bis(2-chloropropenyl) sulfide has been found. Transformations were realized without isolation of the intermediate compounds. The reactivity of 4,5,9,10-tetrahydrothieno[3',4;5,6]cycloocta[1,2-c]thiophene has been studied based on the example of acetylation reaction, and the possibility of obtaining bifunctional derivatives with the participation of both thiophene rings has been shown. The structure of some synthesized compounds has been studied with X-ray diffraction method.