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Synthesis and Transformations of the Adduct of 1-Phenyltricyclo[4.1.0.02,7]heptane with 2-Bromoethanesulfonyl Bromide

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Abstract

The addition of 2-bromoethanesulfonyl bromide to the central C1–C7 bond of 1-phenyltricyclo[4.1.0.02,7]heptane proceeds in a highly anti-stereoselective fashion to form 1 : 1 adducts with the norpinic structure. The action of some bases and nucleophiles on the anti-addition product was studied. It was found that, depending on the reaction conditions, the adduct undergoes solvolysis, 1,2-dehydrobromination, and further addition of nucleophile molecule to the double bond of the vinylsulfonyl moiety.

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Authors and Affiliations

  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. Synthesis and Transformations of the Adduct of 1-Phenyltricyclo[4.1.0.02,7]heptane with 2-Bromoethanesulfonyl Bromide. Russ J Org Chem 56, 746–752 (2020). https://doi.org/10.1134/S1070428020050048

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  • DOI: https://doi.org/10.1134/S1070428020050048

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