A vinylogous dehydration mechanism is suggested for the formation of acepleiadylene from 5, 10-dihydroacepleiadene-5, 10-diol. Support for this mechanism is found in the conversion of 5-(α-hydroxybenzyl) acenaphthene to 5-benzylacenaphthylene by p-toluenesulphonyl chloride in pyridine solution. A hydride transfer mechanism for this reaction is ruled out by the observation that 4-(α-hydroxybenzyl) acenaphthene is not converted to an ...
