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Reactions of Tricyclo[4.1.0.02,7]heptane and 1-Methyltricyclo[4.1.0.02,7]heptane with 2-Bromoethanesulfonyl Bromide

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Abstract

2-Bromoethanesulfonyl bromide reacts with tricyclo[4.1.0.02,7]heptane and 1-methyltricyclo[4.1.0.02,7]heptane according to a radical mechanism to give products of both anti and syn addition across the C1–C7 central bicyclobutane bond having a norpinane (bicyclo[3.1.1]heptane) structure. Treatment of the adducts with triethylamine leads to the formation of vinyl sulfones as a result of 1,2-dehydrobromination, and their reaction with sodium methoxide involves 1,2- and 1,3-dehydrobromination and nucleophilic addition, depending on the substrate structure and reactant ratio.

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  1. Ogarev 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. Reactions of Tricyclo[4.1.0.02,7]heptane and 1-Methyltricyclo[4.1.0.02,7]heptane with 2-Bromoethanesulfonyl Bromide. Russ J Org Chem 56, 1014–1022 (2020). https://doi.org/10.1134/S1070428020060081

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