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Iodine Acetate as a Mild Selective Agent for the Wagner–Meerwein Rearrangement in 3a,6-Epoxyisoindoles

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Chemistry of Heterocyclic Compounds Aims and scope

The iodine-initiated cationic skeletal Wagner–Meerwein rearrangement in tetrahydro-3a,6-epoxyisoindol-1-ones has been studied. It was shown that by the action of iodine acetate in acetic anhydride the reaction proceeds regio- and stereoselectively with the formation of 5-iodo-4,6-epoxycyclopenta[c]pyridin-4-yl acetates. The proposed reagent provides better yields of rearrangement products than those described in the literature.

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Authors and Affiliations

  1. RUDN University, 6 Miklukho-Maklaya St, Moscow, 117198, Russia

    Vladimir P. Zaytsev, Dmitriy F. Mertsalov, Anastasiya M. Trunova, Anastasiya V. Khanova & Eugeniya V. Nikitina

  2. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31/4 Leninskiy prosp, Moscow, 119071, Russia

    Anna А. Sinelshchikova & Mikhail S. Grigoriev

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  1. Vladimir P. Zaytsev
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  2. Dmitriy F. Mertsalov
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  3. Anastasiya M. Trunova
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  4. Anastasiya V. Khanova
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  5. Eugeniya V. Nikitina
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  6. Anna А. Sinelshchikova
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  7. Mikhail S. Grigoriev
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Correspondence to Vladimir P. Zaytsev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 930–935

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Zaytsev, V.P., Mertsalov, D.F., Trunova, A.M. et al. Iodine Acetate as a Mild Selective Agent for the Wagner–Meerwein Rearrangement in 3a,6-Epoxyisoindoles. Chem Heterocycl Comp 56, 930–935 (2020). https://doi.org/10.1007/s10593-020-02752-y

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  • DOI: https://doi.org/10.1007/s10593-020-02752-y

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