Abstract
AbstractImproved preparations of 2,6‐dimethylstyrene (5) and its α‐bromo derivative (10) are described. The Br/Li exchange reaction of 10 provides single crystals of the title compounds 11 or 12, which were characterized as disolvated dimers by X‐ray analyses. A similar dimer persists in diethyl ether, tert‐butyl methyl ether, and toluene at all accessible temperatures, with significant lithiation NMR shifts (relative to 5) partially due to charge delocalization from the sp2‐carbanionic center. Some NMR coupling constants are typical of the dimeric aggregate. The configurational (E,Z) lability is quantified in toluene solution.
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