作者:M.P. Cava、K.E. Merkel、R.H. Schlessinger
DOI:10.1016/s0040-4020(01)96925-x
日期:1965.1
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
有人建议采用乙烯基脱水机理,由5,10-二氢乙酰丙酮-5,10-二醇形成乙酰丙烯。在吡啶溶液中通过对甲苯磺酰氯将5-(α-羟基苄基)ac烯转化为5-苄基ena烯中发现了对该机理的支持。通过观察到在相同条件下4-(α-羟基苄基)ac并没有转化为an衍生物,从而排除了该反应的氢化物转移机理。描述了许多of衍生物的详细合成。