Synthesis and reactions of atropisomeric compounds

CHED 228

Anthony J. Fowler, ajfowler@uncc.edu and Craig A. Ogle, cogle@uncc.edu. Department of Chemistry, University of North Carolina at Charlotte, 9201 University City Blvd, Charlotte, NC 28223
Previously we have reported the synthesis of 1-(3,4,5-trimethoxyphenyl)naphthalene (1), herein we introduce both derivatives and analogues of this compound. Reaction of this compound with n-BuLi/TMEDA has been shown to lithiate at the phenyl ring ortho to the methoxy group (2). Further reaction with any number of groups can give rise to resolvable isomers of the new compound through the induced increase to the energy barrier to rotation around the aryl-aryl bond (3).