La-Activated Bicyclo-oligomerization of Acetylene to Naphthalene

Dilrukshi Hewage, W. Ruchira Silva, Wenjin Cao, Dong Sheng Yang

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

We report the first example of metal-mediated acetylene bicyclopentamerization to form naphthalene in the gas phase. The bicyclic aromatic compound was observed in a complex with La. The La(naphthalene) complex was formed by the reaction of laser-ablated La atoms with acetylene molecules in a molecular beam source and was characterized by mass-analyzed threshold ionization spectroscopy. The bicyclo-oligomerization reaction occurs through sequential acetylene additions coupled with dehydrogenation. Three intermediates in the reaction have been identified: lanthanacyclopropene [La(C2H2)], La(cyclobut-1-en-3-yne) [La(C4H2)], and La(benzyne) [(La(C6H4)]. The metal-ligand bonding in the three intermediates is considerably different from that in the La(naphthalene) complex, as suggested by accurately measured adiabatic ionization energies.

Original languageEnglish
Pages (from-to)2468-2471
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number8
DOIs
StatePublished - Mar 2 2016

Bibliographical note

Publisher Copyright:
© 2016 American Chemical Society.

Funding

We are grateful for the financial support from the National Science Foundation, Division of Chemistry (Chemical Structure, Dynamics, and Mechanisms, Grant CHE-1362102). We also acknowledge additional support from the Kentucky Science and Engineering Foundation. We thank Jack Selegue for helpful discussions about possible reaction pathways for the cyclopentamerization of acetylene.

FundersFunder number
National Science Foundation (NSF)1362102
Department of Chemistry and Division of Medicinal Chemistry and PharmaceuticsCHE-1362102
Kentucky Science and Engineering Foundation

    ASJC Scopus subject areas

    • Catalysis
    • General Chemistry
    • Biochemistry
    • Colloid and Surface Chemistry

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