Chemistry of neopentyl derivatives—II

Add time:07/17/2019    Source:sciencedirect.com

A series of neopentylbenzene derivatives with substituents in 2- and 6-positions has been synthesized. A number of compounds were investigated by dynamic NMR spectroscopy. Restricted rotation was observed in 3-methyl-2-neopentylbenzoic acid and its derivatives. Thermodynamic and Arrhenius parameters were obtained for the restricted rotation of the neopentyl group. An additional Me group in 3-position causes a COOMe group in 2-position to rotate out of the plane of the aromatic ring, and this change is effective in reducing the barrier to rotation of the neopentyl group by about 1 kcal mole−1.

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