101747-07-3

Upstream product

• 100-42-5 styrene 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 2206-94-2 1-acetoxy-1-phenylethene 
• 98-86-2 acetophenone 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 130460-26-3 7a-Hydroxy-2-phenyl-3,4,5,6,7,7a-hexahydro-indole-3a-carboxylic acid ethyl ester 
• 98-86-2 acetophenone 
• 1448863-68-0 ethyl 2-[2-(2,4-dinitrophenyl)hydrazono]-1-(2-oxo-2-phenylethyl)cyclohexanecarboxylate 
• 1448863-66-8 ethyl 1-(4-iodophenyl)-3-phenyl-1,4,4a,5,6,7-hexahydrobenzo[c]pyridazine-4a-carboxylate 
• 1448863-67-9 ethyl 2-(4-iodophenyl)-3-phenyl-2,4a,5,6,7,8-hexahydrobenzo[c]pyridazine-4a-carboxylate 
• 1448863-65-7 ethyl 1-(4-methylphenyl)-3-phenyl-1,4,4a,5,6,7-hexahydrobenzo[c]pyridazine-4a-carboxylate 
• 1448863-64-6 ethyl 1-(2-methylphenyl)-3-phenyl-1,4,4a,5,6,7-hexahydrobenzo[c]pyridazine-4a-carboxylate 
• 1448863-63-5 ethyl 1-(4-methoxyphenyl)-3-phenyl-1,4,4a,5,6,7-hexahydrobenzo[c]pyridazine-4a-carboxylate 
• 1448863-62-4 ethyl 1-(2-methoxyphenyl)-3-phenyl-1,4,4a,5,6,7-hexahydrobenzo[c]pyridazine-4a-carboxylate 
• 1448863-60-2 ethyl 1-(3,4-dichlorophenyl)-3-phenyl-1,4,4a,5,6,7-hexahydrobenzo[c]pyridazine-4a-carboxylate 
• 1448863-61-3 ethyl 2-(3,4-dichlorophenyl)-3-phenyl-2,4a,5,6,7,8-hexahydrobenzo[c]pyridazine-4a-carboxylate 
• 1448863-59-9 ethyl 1-(2-chlorophenyl)-3-phenyl-1,4,4a,5,6,7-hexahydrobenzo[c]pyridazine-4a-carboxylate 
• 1448863-39-5 ethyl 1,3-diphenyl-1,4,4a,5,6,7-hexahydrobenzo[c]pyridazine-4a-carboxylate 
• 1448863-36-2 ethyl 1-(2-oxo-2-phenylethyl)-2-(2-phenylhydrazono)cyclohexanecarboxylate 

Relevant academic research and scientific papers

Formation of δ-Lactones by Cerium-Catalyzed, Baeyer-Villiger-Type Coupling of β-Oxoesters, Enol Acetates, and Dioxygen

Formation of δ-lactones is observed when cyclopentanone-2-carboxylates are converted in a cerium-catalyzed reaction with α-aryl vinyl acetates under oxidative conditions. The products of this transformation possess a 1,4-dicarbonyl constitution together with a quaternary carbon center. Atmospheric oxygen is the oxidant in this process, which can be regarded as ideal from economic and ecological points of view. Further advantages of this new C-C coupling and oxidation reaction are its operational simplicity and the application of nontoxic and inexpensive CeCl3·7 H2O as precatalyst. This so far unprecedented reaction is proposed to proceed via 1,2-dioxane derivatives, which decompose under formation of an oxycarbenium cation in a Baeyer-Villiger-type pathway. This mechanistic picture is supported by the observation that electron-rich (donor substituted or heteroaromatic) enol esters give higher yields than electron deficient congeners. Apart from 1,4-diketones and α-hydroxylated β-oxoesters formed as byproducts, the yields of δ-lactones range from moderate to good (up to 74%).

Synthesis of 1,4-Diketones from β-Oxo Esters and Enol Acetates by Cerium-Catalyzed Oxidative Umpolung Reaction

Cyclic β-oxo esters are converted with enol acetates in a cerium-catalyzed, oxidative Umpolung reaction to furnish 1,4-diketones with up to 95 % yield. Atmospheric oxygen is the oxidant in this process, which can be regarded as ideal from economic and ecological points of view. Further advantages of this new C-C coupling reaction are its operational simplicity and the application of nontoxic and inexpensive CeCl3·7H2O as precatalyst.

Cerium-catalyzed, aerobic oxidative synthesis of 1,2-dioxane derivatives from styrene and their fragmentation into 1,4-dicarbonyl compounds

1,4-Diketones were prepared by cerium-catalyzed oxidative coupling of styrene with molecular oxygen and 1,3-dicarbonyl compounds. This two-step sequence was performed as a one-pot procedure without isolation of the intermediate products. The first step is

Formation of 1,4-diketones by aerobic oxidative C-C coupling of styrene with 1,3-dicarbonyl compounds

(Chemical equation presented). Convenient and direct: 1,4-Dicarbonyl compounds are readily obtained through a one-pot cerium-catalyzed oxidative C-C coupling in the presence of oxygen and subsequent fragmentation. The products are suitable precursors for

Cerium-Catalyzed Reaction of β-Dicarbonyl Compounds with Styrene and Atmospheric Oxygen

The cerium-catalyzed C-C coupling reaction of carbo- and heterocyclic β-dicarbonyl compounds 1 with styrenes 4, using oxygen (air) as the oxidant, at ambient temperature, is reported. The reaction afforded a mixture of diastereoisomeric hydroperoxides 5 w

THE SYNTHESIS AND CHEMISTRY OF AZOLENINES. PART 18. PREPARATION OF 3-ETHOXYCARBONYL-3H-PYRROLES VIA THE PAAL-KNORR REACTION, AND SIGMATROPIC REARRANGEMENTS INVOLVING COMPETITIVE ESTER MIGRATIONS TO C-2, C-4 AND N.

3H-Pyrrole-3-carboxylic esters (4) have been prepared, in some cases together with isomers (5) and (6) having exocyclic double bonds, by cyclization of suitably substituted 2-ethoxycarbonyl-1,4-diketones (1) with liquid ammonia, followed by dehydration of the isolable 2-hydroxy-3,4-dihydro-2H-pyrrole intermediates (2) and (3) with aluminia in boiling solvents.Prolonged heating in toluene or p-xylene converts the 3H-pyrroles (4) quantitatively into isomeric 4-esters (11) and N-esters (13) of 1H-pyrroles via competitive sigmatropic rearrangements.Isolable intermediate 2H-pyrrole-2-carboxylic esters (12) are converted similarly into the same products, under the same conditions.Detection of 3H-pyrroles (4) as intermediates in the latter reaction demonstrates for the first time the reversibility of the thermal 2H-pyrrole to 3H-pyrrole interconversion.