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

Tuyun A. F.

HETEROCYCLES, vol.87, no.12, pp.2589-2598, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 87 Issue: 12
  • Publication Date: 2013
  • Doi Number: 10.3987/com-13-12860
  • Journal Name: HETEROCYCLES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2589-2598
  • Keywords: Thiophene, Nitrothiophene, Dithiolane, Buta-1,3-diene, Nitrobutadienyl Block, POLYHALOGENATED NITROBUTADIENES, N,S-SUBSTITUTED NITRODIENES, NUCLEOPHILIC-SUBSTITUTION, CHEMISTRY, THIOPHENES, REACTIVITY, BUTADIENES, DIENES
  • Istanbul University Affiliated: No

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.