ACTION OF WITTIG‐HORNER REAGENTS ON o-QUINONES

Reactions of α-Diketones ando-Quinones with Phosphorus Compounds

“…The reaction of acenaphthenequinone with triethylphosphonoacetate ( 181 ) in ethanol in the presenceof sodium ethoxide gives the two dimeric products having structures 182 and 183 , respectively …”

The reactions of Wittig-Horner reagents with 1,3-dioxo-?2,?-indanmalononitrile

“…Triethyl phosphonoacetate and diethyl (cyanomethyl)phosphonate were prepared by means of the Michaelis-Ar-buzov reaction [15][16][17] Reaction of Diethyl (Cyanomethyl )phosphonate (1a) with Dicyanomethyleneindene-1,3-dione (2) A solution of 2 mols of sodium ethoxide in absolute ethanol was treated with an equimolar amount of diethyl (cyanomethyl)phosphonate (1a), and then the dicyano compound (2) (1 mol) was added. The resulting reaction mixture was allowed to stir for 4 hours at room temperature.…”

“…Carrying out the reaction using 2 moles of Wittig-Horner reagent 1b instead of 1 mole led to the formation of 4a in good yield. Reasons for structure 4a were as follows: (a) Elemental and mass spectral analyses for compound 4a corresponds to an empirical formula C 24 2 , m), corresponding to the two carbethoxy groups. The two ethoxy groups attached to the phosphorus atom appeared as a triplet centered at 1.25 (6H, CH 3 , t) and as a quintet centered at 4.25 (4H, CH 2 , q).…”

Synthesis and Reactions of Acenaphthenequinones-Part-2. The Reactions of Acenaphthenequinones

“…The adducts 104 were isolated from the reaction of 1 with triethyl phosphonoacetate ( Scheme 27 ) [ 89 ]. The reaction of 1 with a resonance-stabilized phosphorane [ 90 ], such as acetonylidene-, phenacylidene-and p-chlorophenacylidene-phosphoranes afforded the expected α,β-unsaturated ketones 105 .…”