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Harrington LE, Britten JF, McGlinchey MJ. Dimerization of 9-phenylethynylfluorene to di-indeno-naphthacene and dispiro-[fluorene-dihydronaphthacene-fluorene]: an X-ray crystallographic and NMR study. Org Lett. 2004;6(5):787-90doi: 10.1021/ol049967o.
Harrington, L. E., Britten, J. F., & McGlinchey, M. J. (2004). Dimerization of 9-phenylethynylfluorene to di-indeno-naphthacene and dispiro-[fluorene-dihydronaphthacene-fluorene]: an X-ray crystallographic and NMR study. Organic letters, 6(5), 787-90. https://doi.org/10.1021/ol049967o
Harrington, Laura E, et al. "Dimerization of 9-phenylethynylfluorene to di-indeno-naphthacene and dispiro-[fluorene-dihydronaphthacene-fluorene]: an X-ray crystallographic and NMR study." Organic letters vol. 6,5 (2004): 787-90. doi: https://doi.org/10.1021/ol049967o
Harrington LE, Britten JF, McGlinchey MJ. Dimerization of 9-phenylethynylfluorene to di-indeno-naphthacene and dispiro-[fluorene-dihydronaphthacene-fluorene]: an X-ray crystallographic and NMR study. Org Lett. 2004 Mar 04;6(5):787-90. doi: 10.1021/ol049967o. PMID: 14986975.
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Org Lett. 2004 Mar 04;6(5):787-90. doi: 10.1021/ol049967o.

Dimerization of 9-phenylethynylfluorene to di-indeno-naphthacene and dispiro-[fluorene-dihydronaphthacene-fluorene]: an X-ray crystallographic and NMR study.

Organic letters

Laura E Harrington, James F Britten, Michael J McGlinchey

Affiliations

  1. Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, Canada L8S 4M1.

PMID: 14986975 DOI: 10.1021/ol049967o

Abstract

The attempted Diels-Alder reaction between 9-phenylethynylfluorene and tetracyclone yields instead three products resulting from the dimerization of the isomeric allene. The major product is 8,16-diphenyl-diindeno[1,2,3-de:1',2',3'-mn]naphthacene, in which each terminal ring is derived from a fluorenyl unit; aerial oxidation then yields a peroxide. A dihydronaphthacene bearing fluorenyl moieties spiro-bonded at the C(5) and C(11) positions was also identified. The structures of the naphthacenes were elucidated by X-ray crystallography, and a mechanistic rationale is offered. [reaction: see text]

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