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On Radical Reactions of 1-Bromotricyclo[4.1.0.02,7]heptane with Phenylethynyl Sulfones

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Abstract

Phenylethynyl sulfones of the general formula RSO2C≡CPh (R = p-Tol, Ph, CH3) undergo a photochemically induced anti-stereoselective addition to the central C1–C7 bond of 1-bromotricyclo[4.1.0.02,7]heptane to form monoadducts of the bicyclo[3.1.1]heptane (norpinic) series containing a syn-sulfonyl group in position 7 and a phenylethynyl moiety on C6. Treatment of the synthesized adducts with potassium tert-butylate in THF leads to 1,3-dehydrobromination to give sulfonyl-substituted 1-(phenylethynyl)tricyclo[4.1.0.02,7]heptanes.

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  1. Ogarev National Research Mordovia State University, 430005, Saransk, Russia

    S. G. Kostryukov & Yu. Yu. Masterova

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  1. S. G. Kostryukov
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  2. Yu. Yu. Masterova
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Correspondence to S. G. Kostryukov.

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Kostryukov, S.G., Masterova, Y.Y. On Radical Reactions of 1-Bromotricyclo[4.1.0.02,7]heptane with Phenylethynyl Sulfones. Russ J Org Chem 56, 741–745 (2020). https://doi.org/10.1134/S1070428020050036

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