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Chemical Reactions of Spirooxiranes

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Abstract

The review covers the reactivity of spirooxiranes. The characteristic distinction of chemical behavior of this type epoxides from that of epoxycycloalkanes is discussed. In the spirooxiranes unlike epoxycycloalkanes the oxirane and alicyclic fragments are joined by one and not by two common atoms. The spirooxiranes are characterized by enhanced reactivity in the neutral and alkaline media, and also by versatile isomerizations and rearrangements in the presence of acidic catalysts. The relation between the chemical properties of spirooxiranes and the features of their electronic structure was considered. The main reactions of spirooxiranes with reductants, reactants with nucleophilic centers on oxygen, sulfur, carbon, nitrogen, and phosphorus, and with hydrogen halides are analyzed. The isomerization of spirooxiranes into carbonyl compounds and allyl alcohols is discussed. The possibility was considered of formation of the other cyclic systems proceeding from spirooxiranes.

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  1. Dnepropetrovsk State University, Dnepropetrovsk, 49050, Ukraine

    L. I. Kas'yan, A. O. Kas'yan & I. N. Tarabara

  2. Ukrainian State Chemico-technological University, Ukraine

    L. I. Kas'yan, A. O. Kas'yan & I. N. Tarabara

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Kas'yan, L.I., Kas'yan, A.O. & Tarabara, I.N. Chemical Reactions of Spirooxiranes. Russian Journal of Organic Chemistry 37, 1361–1404 (2001). https://doi.org/10.1023/A:1013447910907

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