title: Urotropine isomer (1,4,6,10-tetraazaadamantane): synthesis, structure, and chemistry.
abstract: 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.
authors.affiliation: N.D. Zelinsky Institute of Organic Chemistry , Leninsky prospect 47, 119991, Moscow, Russia.
authors.forename: Artem N
authors.initials: AN
authors.lastname: Semakin
authors.forename: Alexey Yu
authors.initials: AY
authors.lastname: Sukhorukov
authors.forename: Yulia V
authors.initials: YV
authors.lastname: Nelyubina
authors.forename: Yulia A
authors.initials: YA
authors.lastname: Khomutova
authors.forename: Sema L
authors.initials: SL
authors.lastname: Ioffe
authors.forename: Vladimir A
authors.initials: VA
authors.lastname: Tartakovsky