Ruthenocene 1,2-dicarboxylic acid, carboxylic anhydride, and acid chloride: A facile route to metallocene-fused acenequinones

Uttam Raj Pokharel, John P. Selegue, Sean Parkin

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The dehydration of 1′,2′,3′,4′,5′- pentamethylruthenocene-1,2-dicarboxylic acid with acetic anhydride gives 1′,2′,3′,4′,5′-pentamethylruthenocene-1, 2-dicarboxylic anhydride, the first crystallographically characterized, metallocene-fused carboxylic anhydride. Treatment of the diacid with oxalyl chloride/DMF produces its 1,2-diacyl chloride, which is an excellent precursor for AlCl3-promoted double Friedel-Crafts acylation reactions with a variety of arenes, including benzene, toluene, o-xylene, p-dimethoxybenzene, and ferrocene. X-ray structural determinations of an acenequinone and a unique ferrocene/ruthenocene-fused benzoquinone show distortions attributed to strong electron donation from pentamethylruthenocene.

Original languageEnglish
Pages (from-to)3254-3256
Number of pages3
JournalOrganometallics
Volume30
Issue number12
DOIs
StatePublished - Jun 27 2011

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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