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Polycyclic aromatic hydrocarbons by ring-closing metathesis.
J Org Chem. 2005 Oct 14; 70(21):8522-6.JO

Abstract

A strategy for the synthesis of polycyclic aromatic hydrocarbons (PAHs) by the ring-closing olefin metathesis (RCM) of pendant olefins on a phenylene backbone has been developed. RCM of 2,4',6',2' '-tetravinyl-[1,1';3',1' ']terphenyl and 2,2',5',2' '-tetravinyl-[1,1';4',1']terphenyl affords in high yield the isomeric [a,j] and [a,h] dibenzanthracenes, respectively. In contrast with other intramolecular annulation methods, such as Friedel-Crafts acylations, this reaction is completely regioselective. Since RCM is reversible and PAHs are often thermodynamic sinks, this strategy is an effective and general method for the preparation of PAHs. Density functional theory calculations support these results. Carbon disulfide is a suitable solvent for these reactions.

Authors+Show Affiliations

Bonifacio MC
Department of Chemistry, University of Nevada, Reno, Nevada, 89557, USA.
Robertson CR
No affiliation info available
Jung JY
No affiliation info available
King BT
No affiliation info available

MeSH

Carbon DisulfideCyclizationDimerizationMolecular StructureMolybdenumPolycyclic Aromatic HydrocarbonsRutheniumSolvents

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

16209602

Citation

Bonifacio, Margel C., et al. "Polycyclic Aromatic Hydrocarbons By Ring-closing Metathesis." The Journal of Organic Chemistry, vol. 70, no. 21, 2005, pp. 8522-6.
Bonifacio MC, Robertson CR, Jung JY, et al. Polycyclic aromatic hydrocarbons by ring-closing metathesis. J Org Chem. 2005;70(21):8522-6.
Bonifacio, M. C., Robertson, C. R., Jung, J. Y., & King, B. T. (2005). Polycyclic aromatic hydrocarbons by ring-closing metathesis. The Journal of Organic Chemistry, 70(21), 8522-6.
Bonifacio MC, et al. Polycyclic Aromatic Hydrocarbons By Ring-closing Metathesis. J Org Chem. 2005 Oct 14;70(21):8522-6. PubMed PMID: 16209602.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Polycyclic aromatic hydrocarbons by ring-closing metathesis. AU - Bonifacio,Margel C, AU - Robertson,Charles R, AU - Jung,Jun-Young, AU - King,Benjamin T, PY - 2005/10/8/pubmed PY - 2006/6/29/medline PY - 2005/10/8/entrez SP - 8522 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 70 IS - 21 N2 - A strategy for the synthesis of polycyclic aromatic hydrocarbons (PAHs) by the ring-closing olefin metathesis (RCM) of pendant olefins on a phenylene backbone has been developed. RCM of 2,4',6',2' '-tetravinyl-[1,1';3',1' ']terphenyl and 2,2',5',2' '-tetravinyl-[1,1';4',1']terphenyl affords in high yield the isomeric [a,j] and [a,h] dibenzanthracenes, respectively. In contrast with other intramolecular annulation methods, such as Friedel-Crafts acylations, this reaction is completely regioselective. Since RCM is reversible and PAHs are often thermodynamic sinks, this strategy is an effective and general method for the preparation of PAHs. Density functional theory calculations support these results. Carbon disulfide is a suitable solvent for these reactions. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/16209602/Polycyclic_aromatic_hydrocarbons_by_ring_closing_metathesis_ DB - PRIME DP - Unbound Medicine ER -