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JOURNAL ARTICLE
RESEARCH SUPPORT, NON-U.S. GOV'T
C Ar -O Rotamers in 3,3'-Disubstituted BINOL Esters.
Journal of Organic Chemistry 2017 March 18
Rotamers around the CAr -O bond were disclosed in 3,3'-disubstituted BINOL esters by NMR spectroscopy. A bulky R1 group increased the rotational barrier. The pivalate showed two rotamers at 2 °C, and broad signals were observed close to room temperature when R2 = Ph. The highest rotational barrier was recorded for the (tetracyanocyclopentadienyl)carboxylate, and C-O rotamers were present at room temperature. DFT calculations indicated the presence of repulsion between R1 and R2 during rotation of the CAr -O bond.
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