Reaction of cobalt tetracarbonyl hydride with phenylacetylene

T. Michael Bockman, John F. Garst, Ferenc Ungváry

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

In C6H6 or hexane at room temperature, under an atmosphere of CO, excess HCo(CO)4 reacts with phenylacetylene to give ethylbenzene and 2-phenylpropanal, the same products that result from the similar reaction of styrene. This and other evidence show that styrene is an intermediate. However, when phenylacetylene is in large excess, neither ethylbenzene, 2-phenylpropanal, nor styrene is formed in more than trace quantity. Instead, a compound is formed whose spectral properties suggest that it is an alkyl- or acylcobalt carbonyl containing a 1-phenylethenyl group. This compound reacts with HCo(CO)4 to give styrene. CIDNP suggests that the reaction of phenylacetylene with HCo(CO)4 proceeds through radical pairs [1-phenylethenyl··Co(CO)4].

Original languageEnglish
Pages (from-to)41-47
Number of pages7
JournalJournal of Organometallic Chemistry
Volume586
Issue number1
DOIs
Publication statusPublished - Jul 31 1999

    Fingerprint

Keywords

  • Alkenylcobalt carbonyl
  • CIDNP
  • Cobalt tetracarbonyl hydride
  • Free-radical reaction
  • Hydroformylation
  • Phenylacetylene
  • Styrene

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this