The synthesis of new thiosubstituted butadienes, butenynes and butatrienes

Ibis C., BEYAZİT N.

ARKIVOC, vol.2010, pp.244-256, 2010 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 2010
  • Publication Date: 2010
  • Doi Number: 10.3998/ark.5550190.0011.923
  • Journal Name: ARKIVOC
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.244-256
  • Hatay Mustafa Kemal University Affiliated: Yes

Abstract

By treatment of the pentachlorobutadiene 1 and of the tetrachlorobromobutadiene 9 with thiolates in ethanol, a very fast and extensive replacement of chlorine was observed even at room temperature. The reaction of 1 with three molar equivalents of thiolates lead to butadienes with two, three, four and five organylthio groups. Tris(thio)-substituted butadienes 3a-c tetrakis (thio)-substituted butadiene 4a were treated with potassium tert-butoxide to form tris(thio)substituted butatrienyl halide compounds 12a-c and tetrakis(thio)-substituted butatriene 14a, respectively. The butatrienyl halides 12a-c obtained partly isomerizes to give butenynes 13a-c at room temperature and without catalyst.