Quinuclidine Chemistry

Chemistry of quinuclidines as nitrogen bicyclic bridged‐ring structures

“…However, the rates of reaction of alkyl iodides with quinuclidine are higher than with tertiary aliphatic amines. The addition compound of trimethylborane with quinuclidine is more stable than the corresponding adducts of trialkylamines [1]. These results can be explained by the almost total absence of steric hindrance at the nitrogen lone-pair of the bicyclic compound.…”

“…In contrast to other 1-azabicycloalkanes, quinuclidine is notable for its high symmetry and for the insignificant bond strain. The nitrogen lone-pair electrons are sp 3 -hybridized and are not subject to steric crowding [1].…”

“…In condensed benzo-and dibenzoquinuclidine systems, the basicity decreased due to the inductive effect of the benzene rings [1].…”

“…Many papers have been reported so far concerning the synthesis, catalysis or biological activity of quinuclidine (1-azabicyclo[2.2.2]octane) (1) [1], inasmuch as quinuclidine is part of the structure of a number of natural physiologically active compounds, such as cinchona and some indole alkaloids, and synthetic drugs [1][2][3][4][5][6][7][8]. These numerous papers have been occasionally summarized in some monographs [1] and reviews [2,4].…”

“…These numerous papers have been occasionally summarized in some monographs [1] and reviews [2,4]. However, a sufficient number of reviews have not been currently provided.…”