SYNTHETIC EXPLOITATION OF HALOGENATED ALKENES CONTAINING ELECTRON-WITHDRAWING GROUP (EWG): ACCESS TO VALUABLE 2,4-DINITROTHIOPHENES VIA RING-CLOSING AND RING-OPENING/RING-CLOSING PROTOCOLS

Abstract

With the goal of their exploitation for the synthesis of highly functionalized 2,4-dinitrothiophenes, 2-(2,3-dichloro-1,3-dinitroallylidene)-1,3-dithiolane (2), derived from the initial ring-closing of polyhalogenated nitrobutadienic building blocks with 1,2-ethanedithiol, were reacted with secondary amines. After protic work up, highly functionalized 2,4-dinitrothiophenes have been accomplished via ring-opening/ring-closing protocols.