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Updated: Jul 13, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
rac-(Z)-2-(2-Thienylmethylene)-1-azabicyclo[2.2.2]octan-3-ol
Vijayakumar N Sonar1, M Venkatraj, Sean Parkin
1Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA.
Abstract:
The asymmetric unit of the racemic form of the title compound, C(12)H(15)NOS, contains four crystallographically independent molecules. The olefinic bond connecting the 2-thienyl and 1-azabicyclo[2.2.2]octan-3-ol moieties has Z geometry. Strong hydrogen bonding occurs in a directed co-operative O-H...O-H...O-H...O-H R(4)(4)(8) pattern that influences the conformation of the molecules. Co-operative C-H...pi interactions between thienyl rings are also present. The average dihedral angle between adjacent thienyl rings is 87.09 (4) degrees.
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