o-Tolyl-substituted tetrahydrofurans undergo highly regioselective ring opening with the concomitant formation of new C-C bonds as the result of a lateral lithiation reaction. This reaction provides a new method for the synthesis of functionalised primary alcohols and can be run directly in protic eutectic mixtures as benign reaction media at 0 °C and under air, competitively with protonolysis.
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Sassone et al. (2015) studied this question.
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