Azatriquinanes: Synthesis, Structure, and Reactivity.
Azatriquinane, a tricyclic amine with rigid, hemispherical topology, is synthesized in six steps from pyrrole. This first example of a [2.2.2]cyclazine can be oxidatively dimerized to a novel, highly strained heptacycle or oxidized with chlorine to give an azatriquinacene, a theoretical precursor to diazadodecahedrane via Woodward dimerization.
Hext
Nicholas M.
NM
Department of Chemistry, University of Nottingham, Nottingham NG7 2RD, U.K., and Department of Chemistry, University of Wales Cardiff, P.O. Box 912, Cardiff CF1 3TB, U.K.
Hansen
Jens
J
Blake
Alexander J.
AJ
Hibbs
David E.
DE
Hursthouse
Michael B.
MB
Shishkin
Oleg V.
OV
Mascal
Mark
M