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[1+1]-cyclization of 4-(1-adamantyl)-2,6-diformylphenol with 1,3-bis(aminoalkyl)adamantanes

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Abstract

Selective [1+1]-cyclization of 4-(1-adamantyl)-2,6-diformylphenol with 1,3-bis(aminoalkyl)-adamantane under high dilution conditions in methanol was used to synthesize a new type of adamantine araliphanes, macrocyclic nitrogen-containing compounds with phenolic and adamantane fragments incorporated in the macroring. The [1+1]-cyclization reaction proceeds unusually to form, along with macrocyclic Schiff bases, methanol addition products at one of the N=CH groups of these compounds. The [1+1]-cyclization pattern is shown to depend on the reaction conditions and the structure of the starting diamine.

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Authors and Affiliations

  1. Lomonosov Moscow State University, Leninskie Gory, Moscow, 119992, Russia

    E. A. Shokova & V. V. Kovalev

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  1. E. A. Shokova
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  2. V. V. Kovalev
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Correspondence to E. A. Shokova.

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Original Russian Text © E.A. Shokova, V.V. Kovalev, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 4, pp. 633–641.

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Shokova, E.A., Kovalev, V.V. [1+1]-cyclization of 4-(1-adamantyl)-2,6-diformylphenol with 1,3-bis(aminoalkyl)adamantanes. Russ J Gen Chem 78, 614–622 (2008). https://doi.org/10.1134/S1070363208040178

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  • DOI: https://doi.org/10.1134/S1070363208040178

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