1601-09-8

Upstream product

• 3375-38-0 1,4-dibenzoylbutane 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 111-50-2 Adipic acid dichloride 
• 71-43-2 benzene 
• 59875-94-4 1,1-dibenzoylpropane 
• 4851-15-4 2--1-phenyl-cyclopent-1-en 

Downstream Products

• 861591-36-8 (1-methyl-2-phenylcyclopent-2-en-1-yl)(phenyl)methanone 
• 4851-21-2 1-Phenyl-2--cyclopent-1-en 
• 4851-12-1 2-Benzimidoyl-1-phenyl-cyclopent-1-en 
• 4851-18-7 2--1-phenyl-cyclopent-1-en 
• 4851-41-6 2--1-phenyl-cyclopent-1-en 
• 4851-15-4 2--1-phenyl-cyclopent-1-en 
• 118543-45-6 4-benzoyl-5-oxo-5-phenyl-valeric acid 
• 110-15-6 succinic acid 
• 65-85-0 benzoic acid 
• 4810-11-1 1-phenyl-5-methylcyclopentene 
• 1601-04-3 phenyl-(2-phenyl-cyclopent-1-enyl)-ketone 
• 4851-31-4 2-(N-Benzoyl-benzimidoyl)-1-phenyl-cyclopent-1-en 
• 4851-32-5 2--1-phenyl-cyclopent-1-en 
• 4851-33-6 2--1-phenyl-cyclopent-1-en 

Relevant academic research and scientific papers

Iodonium-Catalyzed Carbonyl-Olefin Metathesis Reactions

The carbonyl-olefin metathesis reaction has become increasingly important in organic synthesis due to its versatility in functional group interconversion chemistry. Recent developments in the field have identified a number of transition-metal and organic Lewis acids as effective catalysts for this reaction. Herein, we report the use of simple organic compounds such as N-iodosuccinimide or iodine monochloride to catalyze the carbonyl-olefin metathesis process under mild reaction conditions. This work broadens the scope of this chemical transformation to include iodonium sources as simple and practical catalysts.

Hydrogen Bonding Networks Enable Br?nsted Acid-Catalyzed Carbonyl-Olefin Metathesis**

Synthetic chemists have learned to mimic nature in using hydrogen bonds and other weak interactions to dictate the spatial arrangement of reaction substrates and to stabilize transition states to enable highly efficient and selective reactions. The activation of a catalyst molecule itself by hydrogen-bonding networks, in order to enhance its catalytic activity to achieve a desired reaction outcome, is less explored in organic synthesis, despite being a commonly found phenomenon in nature. Herein, we show our investigation into this underexplored area by studying the promotion of carbonyl-olefin metathesis reactions by hydrogen-bonding-assisted Br?nsted acid catalysis, using hexafluoroisopropanol (HFIP) solvent in combination with para-toluenesulfonic acid (pTSA). Our experimental and computational mechanistic studies reveal not only an interesting role of HFIP solvent in assisting pTSA Br?nsted acid catalyst, but also insightful knowledge about the current limitations of the carbonyl-olefin metathesis reaction.

AuCl3-Catalyzed Ring-Closing Carbonyl–Olefin Metathesis

Compared with the ripeness of olefin metathesis, exploration of the construction of carbon–carbon double bonds through the catalytic carbonyl–olefin metathesis reaction remains stagnant and has received scant attention. Herein, a highly efficient AuCl3-catalyzed intramolecular ring-closing carbonyl–olefin metathesis reaction is described. This method features easily accessible starting materials, simple operation, good functional-group tolerance and short reaction times, and provides the target cyclopentenes, polycycles, benzocarbocycles, and N-heterocycle derivatives in good to excellent yields.

Carbonyl-Olefin Metathesis Catalyzed by Molecular Iodine

The carbonyl-olefin metathesis reaction could facilitate rapid functional group interconversion and allow construction of complicated organic structures. Herein, we demonstrate that elemental iodine, a very simple catalyst, can efficiently promote this chemical transformation under mild reaction conditions. Our mechanistic studies revealed intriguing aspects of the activation mode via molecular iodine and the iodonium ion that could change the previously established perception of catalyst and substrate design for the carbonyl-olefin metathesis reaction.

Tropylium-promoted carbonyl-olefin metathesis reactions

The carbonyl-olefin metathesis (COM) reaction is a highly valuable chemical transformation in a broad range of applications. However, its scope is much less explored compared to analogous olefin-olefin metathesis reactions. Herein we demonstrate the use of tropylium ion as a new effective organic Lewis acid catalyst for both intramolecular and intermolecular COM and new ring-opening metathesis reactions. This represents a significant improvement in substrate scope from recently reported developments in this field.

α-Carbonyl Cations in Sulfoxide-Driven Oxidative Cyclizations

The selective, metal-free generation of α-carbonyl cations from simple internal alkynes was accomplished by the addition of a sulfoxide to a densely substituted vinyl cation. The high reactivity of the α-carbonyl cations was found to efficiently induce hydrogen and even carbon shift reactions with unusual selecivities. Complex compounds with highly congested tertiary and all-carbon-substituted quartenary carbon centers can thus be accessed in a single step from simple precursors. Mechanistic analysis strongly supports the intermediacy of the title compounds and provides a simple predictive scheme for the migratory aptitude of different substituents.

AlCl3-mediated aldol cyclocondensation of 1,6- and 1,7-diones to cyclopentene and cyclohexene derivatives

Exactly 1/3 mol of AlCl3 is sufficient to cyclize 1 mol of 1,?-dibenzoylbutane (or pentane) to a cyclopentenone (or hexenone) derivative in high yield at room temperature in 40 min to several hours. This condensation is driven by removing elements of water as HCl and Al(OH)3, and the product enones are exclusively unconjugated, unlike the base-catalyzed condensations providing thermodynamically more stable conjugated enones.