Reaction of (μ-S)2Fe2(CO)6 dianion with 1,2-vinyl and aryl diiodides

Richard S. Glass, Maya S. Singh

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

The inorganic dithiolate, (μ-S)2Fe2(CO) 6 2-, reductively deiodinates trans-1,2-diiodo-1,2- diphenylethene to afford diphenylacetylene in 79% yield. Reaction of (μ-S)2Fe2(CO)6 2- with 1,2-diiodobenzene and 2,3-diiodotoluene results in the formation of the benzenedithiolate complex (μ-S)2Fe2(CO)6 and toluenedithiolate complex (μ-S2C6H4Me) Fe2(CO)6 in 42% and 48% isolated yields, respectively. These reactions appear to involve reductive deiodination of 1,2-diiodobenzene and 2,3-diiodotoluene with (μ-S)2Fe2(CO)6 2- to the corresponding benzynes followed by trapping with the concomitantly formed disulfide (μ-S2)Fe2(CO) 6, to give the observed complexes. As such, these reactions involve the first examples of thermal [2+2] cycloaddition of benzyne to the S-S bond of an inorganic disulfide. Although the reaction was not observed on treatment of other substituted 1,2-diiodobenzenes, 1,2,4,5-tetraiodobenzene was monodeiodinated to 1,2,4-triiodobenzene in 62% isolated yield.

Original languageEnglish (US)
Pages (from-to)185-190
Number of pages6
JournalArkivoc
Volume2005
Issue number6
StatePublished - May 5 2005

Keywords

  • Benzyne
  • Dinuclear iron complexes
  • Reductive deiodination
  • μ-dithiolato ligands

ASJC Scopus subject areas

  • Organic Chemistry

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