Electrophilic additions to tetradehydrodianthracene
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10
摘要：
5,12:6,11-Di[1,2]benzenodibenzo[a,e]cyclooctene (tetrade-hydrodianthracene, TDDA) ( 1 ) reacts with halogens to give transannular ( anti ) 4, 5 and ring-opened ( 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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DOI：
10.1002/jlac.1995199507170
被引量：
年份：
2010
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