Abstract
The first conformational analysis of a bicyclo[4.4.1]undecan-11-one system (1) is presented. Based on low-temperature 13C NMR line-broadening measurements and an X-ray structure of the 1,6-dibromo derivative (2), this ketone adopts a chiral conformation with approximate C2 symmetry about an axis containing the >C=0 bond. The observed NMR line-broadening results are consistent with a dynamic interchange of M and P enantiomeric C2 conformations, or expressed another way, the "effective" development of an additional Cs symmetry plane bisecting the molecule at right angles to the plane containing the one carbon bridge (overall average C2v symmetry). This process has a ΔH barrier of 42 kJ mol1 for ketone 1 (43 kJ mol1 for 2).Key words: bicyclo[4.4.1]undecan-11-one, conformational analysis, NMR line broadening, X-ray structure, enantiomers.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
