Rotamers around the C-O bond were disclosed in 3,3'-disubstituted BINOL esters by NMR spectroscopy. A bulky R group increased the rotational barrier. The pivalate showed two rotamers at 2 °C, and broad signals were observed close to room temperature when R = 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 R and R during rotation of the C-O bond.
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| http://dx.doi.org/10.1021/acs.joc.6b03035 | DOI Listing |
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