STUDIES ON PHOSPOHNIUM YLIDES-XIX. REACTIONS OF CYANOMETHYLENETRIPHENYLPHOSPHORANE WITH CERTAIN DICARBONYL COMPOUNDS

Cyanomethylenetriphenylphosphorane (1) reacted with 1,4-naphthoquinone 1 to give the new ylid-phosphorane adduct 4 and the dimeric product 5. Reaction of acenaphthenequinone (2) with phosphorus ylide I afforded compounds 6 and 7. On the other hand, ylide I reacts with phenanthrenequinone (3) yielding adducts 8, 9 and 10, respectively. Structural reasoning for the new products was based on compatible analytical and spectral data (IR, 1H, 31P-NMR and MS). The mechanism that accounts for the formation of the new adducts is discussed.