O. Tsuge, M. Tashiro, I. Shinkai
1969
Citations
0
Influential Citations
17
Citations
Journal
Bulletin of the Chemical Society of Japan
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 studi...