Coupling reactions of Fe(benzyne)+ and Fe(naphthyne)+ in the gas phase

Kan, Steven Z.; Xu, Young C.; Chen, Quan; Freiser, Ben S.

doi:10.1002/(sici)1096-9888(199712)32:12<1310::aid-jms591>3.0.co;2-6

J. Mass Spectrom.

1997

DOI: 10.1002/(sici)1096-9888(199712)32:12<1310::aid-jms591>3.0.co;2-6

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Coupling reactions of Fe(benzyne)+ and Fe(naphthyne)+ in the gas phase

Steven Z. Kan¹,

Young C. Xu²,

Quan Chen³

et al.

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Cited by 7 publications

(1 citation statement)

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“…La(benzyne) interacts further with two additional acetylene molecules to form the La(naphthalene) product. Metal–benzyne complexes are very reactive and have been used in cycloadditions of alkynes and alkenes in both solution ,,− and the gas phase , to form polycyclic compounds. The cycloaddition reactions of metal–benzyne complexes with alkynes (or alkenes) have been proposed to occur through insertion of the unsaturated molecules into metal–carbon bonds .…”

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La-Activated Bicyclo-oligomerization of Acetylene to Naphthalene

et al. 2016

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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.

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La-Activated Bicyclo-oligomerization of Acetylene to Naphthalene

et al. 2016

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Mechanistic Aspects of the Gas‐Phase Reactions of Halobenzenes with Bare Lanthanide Cations: A Combined Experimental/Theoretical Investigation

Zhou

Schlangen

Schwarz

2014

Chemistry A European J

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The gas-phase reactions of chlorobenzene with all atomic lanthanide cations Ln(+) (except Pm(+) ) have been investigated by using Fourier transform ion cyclotron resonance mass spectrometry in conjunction with density functional theory calculations. According to the latter, a direct chlorine transfer to the lanthanide cation, which has been observed previously for fluorine abstraction from fluorobenzene, is not operative for the C6 H5 Cl/Ln(+) couples; rather, chlorine transfer proceeds through an initial coordination of the lanthanide cation to the aromatic ring of the substrate. Both, the product distribution and the chlorine abstraction efficiencies are affected by the bond dissociation energy (BDE(Ln(+) Cl)) as well as the promotion energies of Ln(+) to attain a 4f(n) 5d(1) 6s(1) configuration. In addition, mechanistic aspects of some CH and CC bond activations are presented. Where appropriate, comparison with the previously studied C6 H5 F/Ln(+) systems is made.

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Gas‐phase ion chemistry in organometallic systems

Operti

Ragazzoni

2005

Mass Spectrometry Reviews

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This review essentially deals with positive ion/molecule reactions occurring in gas-phase organometallic systems, and encompasses a period of time of approximately 7 years, going from 1997 to early 2004. Following the example of the excellent review by Eller & Schwarz (1991; Chem Rev 91:1121-1177), in the first part, results of reaction of naked ions are presented by grouping them according to the neutral substrate, while in the second part, ligated ions are grouped according to the different ligands. Whenever possible, comparison among similar studies is attempted, and general trends of reactivities are evidenced.

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Coupling reactions of Fe(benzyne)+ and Fe(naphthyne)+ in the gas phase

Cited by 7 publications

References 5 publications

La-Activated Bicyclo-oligomerization of Acetylene to Naphthalene

La-Activated Bicyclo-oligomerization of Acetylene to Naphthalene

Mechanistic Aspects of the Gas‐Phase Reactions of Halobenzenes with Bare Lanthanide Cations: A Combined Experimental/Theoretical Investigation

Gas‐phase ion chemistry in organometallic systems

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