16691-78-4

Upstream product

• 16691-79-5 2,5-bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone 
• 35044-04-3 5-Hydroxy-2-methoxy-4,5-diphenyl-cyclopenta-1,3-diene-1,3-dicarboxylic acid dimethyl ester 
• 1830-54-2 3-oxopentanedioic acid dimethyl ester 
• 134-81-6 benzil 

Downstream Products

• 35044-08-7 2-Ethoxy-5-hydroxy-4,5-diphenyl-cyclopenta-1,3-diene-1,3-dicarboxylic acid dimethyl ester 
• 16691-79-5 2,5-bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone 
• 35044-02-1 5-Ethoxy-2-hydroxy-4,5-diphenyl-cyclopenta-1,3-diene-1,3-dicarboxylic acid dimethyl ester 
• 35044-03-2 2,5-Dimethoxy-4,5-diphenyl-cyclopenta-1,3-diene-1,3-dicarboxylic acid dimethyl ester 
• 35082-64-5 2-Hydroxy-5-methoxy-4,5-diphenyl-cyclopenta-1,3-diene-1,3-dicarboxylic acid dimethyl ester 
• 35044-04-3 5-Hydroxy-2-methoxy-4,5-diphenyl-cyclopenta-1,3-diene-1,3-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

Pericyclic reactions of cyclopentadienones with nonactivated olefins in phenolic solvents. Enhancement of the reactivity and periselectivity

The solvent effect of phenols on the reactivity and periselectivity for the pericyclic reactions of cyclopentadienones with olefins involving conjugated medium-ring polyenes has been investigated. The use of phenols as a solvent accelerates tile reaction rates of cycloadditions of cyclopentadienones with nonactivated olefins. In the reaction of cycloheptatriene in p-chlorophenol, the exo [4+6]π cycloadduct was produced predominantly, in which a 15-fold increase of the reaction rate was observed as compared with that in benzene. The [3,3]-sigmatropy and decarbonylation of the primary cycloadducts were also accelerated by phenols. The possible role of phenols is discussed on the basis of kinetic and molecular orbital (MO) calculation data.

One pot synthesis of 1,4-dicarboxymethyl-2,3-diphenylnaphthalene

Benzene 2 from aprotic diazotization of anthranilic acid 1 with isoamylnitrite and subsequent thermal decomposition of the resulted benzenediazonium-2-carboxylate (in situ), has been reacted with 2,5-dicarbomethoxy-3,4-diphenylcyclopentadienone 3 in 1,2-d

Steric and electronic effects on the Weiss reaction. Isolation of 1:1 adducts

The mechanism of the Weiss reaction has been studied with respect to the intermediacy of 4-hydroxycyclopent-2-en-1-ones (1:1 adducts) in this process. Analysis of these experiments provides additional evidence that 4-hydroxycyclopentenones are indeed key intermediates in the Weiss reaction. Based on the reaction of dimethyl 3-oxoglutarate with benzil, pyridil, thenil, furil and phenanthrenequinone, steric effects play the major role in the overall success of this condensation to provide substituted cis-bicyclo[3.3.0]octane-3,7-diones. Moreover a trihydroxyindene [5.6] system (see 26) has been isolated for the first time under the Weiss conditions which provides additional support for the existence of cyclopentenone intermediates in this process.