Tetrahedron

Pleiadene systems—II: On the mechanism of acepleiadylene formation—a vinylogous elimination in the acenaphthene series

MP Cava, KE Merkel, RH Schlessinger

Index: Cava,M.P. et al. Tetrahedron, 1965 , vol. 21, p. 3059 - 3064

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Citation Number: 13

Abstract

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 ...