Studies of Acenaphthene Derivatives. XVI. The Wittig Reaction with Acenaphthenequinone

Publisher Website
Google Scholar
Abstract
The reactions of acenaphthenequinone (III) with several Wittig reagents have been studied. When III was reacted with equimolar amounts of benzylidenetriphenylphosphoranes (IV) at room temperature, the corresponding benzylideneacenaphthenones (V) were obtained in fairly good yields, but the reactions of benzil and phenanthrenequinone with IV did not take place under similar conditions. The reaction of III with two equivalents of IV under severe conditions afforded only V, and no dibenzylidene compounds were obtained. The reaction of III with resonance-stabilized phosphoranes, such as acetonylidene-, phenacylidene- and p-chlorophenacylidenephosphoranes, afforded the expected α,β-unsaturated ketones. In the reaction with ethoxycarbonylmethylenephosphorane, two stereo-isomeric ethoxycarbonylmethyleneacenaphthenones, which were also obtained from the reaction with diethyl ethoxycarbonylmethylphos-phonate, were formed. The structures of the isomers were confirmed on the basis of NMR, UV, and mass spectral studies. Methylenephosphorane reacted with III to give methyleneacena-phthenone in a poor yield. On the contrary, the reaction with ethylidenephosphorane gave bis-2,2′-methyleneacenaphthenone, which was also formed by the reaction of acenaphthenone with glyoxal, in a good yield.

This publication has 4 references indexed in Scilit: