π-Complexes of Lignols with Manganese(I) and Ruthenium(II)

Didier Morvan, Thomas Rauchfuss, Scott R. Wilson

Research output: Contribution to journalArticlepeer-review

Abstract

In view of contemporary interest in lignocellulose, we report the synthesis, structures, and preliminary reactivity of the first π-complexes of the lignin monomers (lignols). Initial studies with guaiacol demonstrated that it binds only weakly to Mo(CO) 3 but [Mn(CO) 3(guaiacol)] BF 4 is robust. Related adducts with the cinnamyl alcohol derivatives, which are more closely related to the lignols, were unstable. From [Cp *Ru(MeCN) 3]PF 6, however, we generated the complete series of π-lignol complexes, including those from coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol as well as derivatives of ferulic and cinnamic acids. From a model dilignol derived from guaiacol and coniferyl alcohol was generated the expected mixture of π-complexes. Competition studies suggest that the allyl alcohol group on lignols does not influence the rate of π-complexation. Competition studies showed that [Cp *Ru(methylferulate)] + hydrolyzes faster than the free ester.

Original languageEnglish (US)
Pages (from-to)3161-3166
Number of pages6
JournalOrganometallics
Volume28
Issue number11
DOIs
StatePublished - Jun 8 2009

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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