Abstract
Abstract5,12:6,11âDi[1,2]benzenodibenzo[a,e]cyclooctene (tetradeâhydrodianthracene, TDDA) (1) reacts with halogens to give transannular (anti) 4, 5 and ringâopened (syn) products 6, 7. The product ratio shows a remarkable solvent dependence. Solvents of medium polarity favor anti addition, whereas syn addition is observed both with increasing and decreasing polarity. For instance, chlorine in toluene adds 100% syn, in dichloroethane 56 % anti, and in trifluorethanol again 100% syn. It is concluded that, depending on solvent polarity, three different mechanisms for electrophilic addition are operative.
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