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Cyclization reactions of long-lived 10,10-dimethyl-9-phenylethynyl-9,10-dihydrophenanthren-9-yl cation

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Abstract

According to the NMR data, long-lived 10,10-dimethyl-9-phenylethynyl-9,10-dihydrophenanthren-9-ylium in acid medium undergoes cyclization whose direction is determined by the acidity of the medium. The cyclization in HSO3F-SbF5 superacid involves the aromatic ring in the phenanthrene core as nucleophilic component and yields 5a,6-dimethyl-4-phenyl-4,5,5a,6-tetrahydroacephenantrylene-4,6-bis(ylium). In trifluoroacetic acid the nucleophilic component is the side-chain phenyl group, and the cyclization product is neutral 8b,14b-dimethyl-8b,14b-dihydrobenzo[g]chrysen-10-yl trifluoroacetate. Both cyclization directions are observed in moderate-strength trifluoromethanesulfonic acid.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    G. E. Sal’nikov, A. M. Genaev, V. A. Bushmelev & V. G. Shubin

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  1. G. E. Sal’nikov
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  2. A. M. Genaev
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  3. V. A. Bushmelev
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  4. V. G. Shubin
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Correspondence to A. M. Genaev.

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Original Russian Text © G.E. Sal’nikov, A.M. Genaev, V.A. Bushmelev, V.G. Shubin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 9, pp. 1328–1336

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Sal’nikov, G.E., Genaev, A.M., Bushmelev, V.A. et al. Cyclization reactions of long-lived 10,10-dimethyl-9-phenylethynyl-9,10-dihydrophenanthren-9-yl cation. Russ J Org Chem 49, 1313–1321 (2013). https://doi.org/10.1134/S1070428013090121

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  • DOI: https://doi.org/10.1134/S1070428013090121

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