Urotropine Isomer (1,4,6,10-Tetraazaadamantane): Synthesis, Structure, and Chemistry

The first synthesis of 1,4,6,10-tetraazaadamantane, the C3v-symmetrical structural isomer of urotropine (1,3,5,7-tetraazaadamantane), and a series of its derivatives is reported. X-ray and quantum-chemical studies revealed remarkable distinctions in structures of urotropine and “isourotropine” catio...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-07, Vol.79 (13), p.6079-6086
Main Authors: Semakin, Artem N, Sukhorukov, Alexey Yu, Nelyubina, Yulia V, Khomutova, Yulia A, Ioffe, Sema L, Tartakovsky, Vladimir A
Format: Article
Language:English
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Summary:The first synthesis of 1,4,6,10-tetraazaadamantane, the C3v-symmetrical structural isomer of urotropine (1,3,5,7-tetraazaadamantane), and a series of its derivatives is reported. X-ray and quantum-chemical studies revealed remarkable distinctions in structures of urotropine and “isourotropine” cations, probably arising from different types of hyperconjugation between lone electron pairs of nitrogen atoms and σ*C–N orbitals in these heterocage systems. Since substitution at bridge and bridgehead nitrogen atoms can be easily introduced, 1,4,6,10-tetraazaadamantane may be considered as a new rigid multivalent (3 + 1) scaffold for the design of functional molecules and materials.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5007703