F. Barba

A New Synthesis of Trans-Biphthalyl

Abstract Sym-phthaloyl chloride under controlled cathodic reduction is converted into trans-[1(3H)-isobenzofuranone, 3-(3-oxo-1(3H)-isobenzofuranylidene)]: trans-biphthalyl in 65% yield.

Cathodic reduction of aromatic halides. an evidence for an ionic mechanism

Abstract A study on the cathodic reduction of the C-X bond in aryl vicinal dihalides and monohalides is made, demostrating in an unequivocal way the presence in all the cases of aryl anion intermediates.

Electrochemical reduction of phthalyl chloride. A new route for the synthesis of 3-substituted phthalides

Abstract The cathodic reduction, under various conditions, of phthalyl chloride enables efficient synthesis of (E)-[1,1′]biisobenzofuranyliden-3,3′-dion (4), [2]-benzopyrano [4,3-c]-[2]benzopyrano-6, 12-dione (7), 3-chlorophthalide (8), phtalide (9), or (E)-3[α-(benzoyloxy) benzylidene] phthalide (12); the structure of the latter compound was confirmed by X-ray crystallography.

A Convenient Synthesis of 3,6-Diarylpyridazines

Abstract Cathodic reductions of phenacyl bromides semicarbazones lead to 1,4-diaryl-1,4-butanedione disemicarbazones which give the corresponding 3,6-diarylpyridazines directly by heating.

Facile High Yield Synthesis of Enediol Diesters

Abstract Cathodic reductions of diaryl-l,2-diketones are carried out in the presence of acylating reagents. The respective enediol diesters are obtained in high yields. The products are formed by reaction of electro-generated intermediates with the acylating agents.

Cathodic reduction of cinnamoyl chloride

Abstract The electrolysis of cinnamoyl chloride in dry acetone anhydrous lithium perchlorate is carried out under controlled cathodic potential on a preparative scale. The ketonic reaction products are identified and their formation is rationalized through the electrogeneration of cinnamoyl free radical, hydrogen abstraction and dimerization of the aldoketene intermediate.

5-cyclopentyl-5-hydroxypentanoic and 4-(2′-hydroxycyclohexyl)-butanoic acids lactones obtention by anodic oxidation of 1-decalone

Abstract The 1-decalone anodic oxidation products in alkaline hydroalcoholic medium with platinum anode are identified. The 5-cyclopentyl-5-hydroxypentanoic acid lactone formation evidence a ring contraction process through a carbocationic intermediate.

Cathodic reduction of phenacyl bromide

Abstract The cathodic reduction of phenacyl bromide yield different products when the electrolysis is carried out in dimethylformamide or methanol. The formation of products is rationalized.

Electrochemical methoxylation of acenaphthylene. A stereoselective effect of anode material

Abstract The electrolyses of acenaphthylene solutions in methanol—sodium methoxide carried out at a constant current intensity yield cis and rans -1,2-acenaphthenediol dimethyl ethers. The relative proportion of stereoisomers changes clearly when using platinum or carbon as anodes.

Cathodic reduction of α-bromopropiophenone in an aprotic medium

Abstract The cathodic reduction in an aprotic medium of α-bromopropiophenone produces 1,4-diphenyl-2,3,-dimethyl-1,4-butanedione. This product is transformed by dehydration in 2,5-diphenyl-3,4-dimethylfuran. The reduction process is rationalized via anionic intermediates.