72774-01-7

Upstream product

• 530-48-3 1,1-Diphenylethylene 
• 604-44-4 4-chloronaphthalen-1-ol 
• 71-43-2 benzene 
• 606-40-6 2-chloro-1-naphthol 
• 10443-43-3 1-chloro-4-methoxynaphthalene 
• 328-50-7 α-ketoglutaric acid 

Relevant academic research and scientific papers

Photoredox-Catalyzed Dimerization of Arylalkenes via an Oxidative [4+2] Cycloaddition Sequence: Synthesis of Naphthalene Derivatives

We report a radical cation [4+2] annulation of arylalkenes to afford naphthalene derivatives using an organic photosensitizer (9-mesityl-10-methylacridinium perchlorate) under visible light photocatalysis. In the presence of oxygen (in the air), the oxidative dimerization/intramolecular [4+2] cycloaddition of two alkene molecules provides 3,4-dihydronaphthalen-1(2H)-ones in good to high yields. Under a nitrogen atmosphere, (dihydro)naphthalenes were attained in moderate to excellent yields by using Selectfluor as the oxidant. The transformation proceeds via a tandem dimeric electrophilic addition/Friedel–Crafts cyclization/radical coupling/elimination sequence. This approach represents a mild and straightforward assembly of the naphthalene skeleton using a visible light photocatalytic cascade strategy. (Figure presented.).

A succinct synthesis of the vaulted biaryl ligand vanol via a dienone-phenol rearrangement

Vanol is a member of the vaulted biaryl family of ligands and it has been proven to be very effective in a number of asymmetric catalytic reactions. The previous synthesis of vanol, while effective, is limited by the cost of reagents involved. The present work evaluates three different approaches to the synthesis of 3-phenyl-1-naphthol, a key intermediate in the synthesis of vanol. The first approach has its key step as the Michael addition of a benzyl Grignard to methyl cinnamate. In the second approach the key step is the first step, a Reformatsky reaction of ethyl bromoacetate and deoxybenzoin. The final and most-efficient approach involves a dienone-phenol rearrangement of a 4-aryl-1-tetralenone generated in-situ from the reaction of 4-chloro-1-naphthol with AlCl3 and benzene, and preliminary results are reported on the extension of this method to substituted vanol derivatives.

REACTION OF PHENOLS AND THEIR DERIVATIVES WITH AROMATIC COMPOUNDS IN THE PRESENCE OF ACIDIC AGENTS. XII. MECHANISM OF CONDENSATION OF 1-NAPHTHOL DERIVATIVES WITH AROMATIC COMPOUNDS

The mechanism of the condensation of 1-naphthol and a series of its derivatives with aromatic compounds is examined.It is shown that the C,C-diprotonated forms of 1-naphthols or the analogous mono-C-protonated complexes of the tautomeric keto forms of the

Substituent-Dependent Electron-Transfer Induced Photooxygenation of 1,1-Diarylethylenes

Rates and products of 9,10-dicyanoanthracene-sensitized photooxygenations of 1,1-diarylethylenes (1a-r) in acetonitrile were studied.If at least one of the aryl groups carries an electron-donating substituent at the para (or ortho) position (1a-l), 3,3,6,6-tetraaryl-1,2-dioxanes (2a-l) are generated in high yields (85-100percent).Benzophenones (3) are the only other observable products. 1,1-Diphenylethylene (1n) and its m-methoxy (1m), p-chloro (1o,p), and p-nitro (1q,r) derivatives, however, yield mainly benzophenones (3m-r) (>50percent) (the p-nitro compounds only in the presence of biphenyl). 1,2-Dioxanes (2m-p), cyclobutanes (4n-p), and α-tetralones (5m-o) are obtained as side products.Dioxanes, benzophenones, and α-tetralones are products of electron-transfer induced oxygenations involving triplet ground-state molecular oxygen, 3O2.Singlet molecular oxygen, O2(1Δg), contributes to the benzophenone formation from strongly electron-donor substituted diarylethylenes.An exception is the most powerful electron-donor substituted diarylethylene 1a, with which O2(1Δg) undergoes an electron-transfer reaction affording dioxane 2a.Dioxane formation proceeds via free-radical cations 1.+, which enter into a chain reaction with 1, 3O2, and another molecule of 1 to yield dioxane 2 and a new radical cation 1.+ that maintains the chain reaction.The efficiency of this chain process, however, is found to be several orders of magnitude smaller than expected.To explain this result, a 1,6-biradical .1-1-O2. is proposed to be generated in this chain reaction as the product-determining intermediate that predominantly fragments into 3O2 and two molecules of 1.Cyclization to dioxane 2 and transformation to benzophenone 3 occur at presumably less than 0.1percent from this biradical.The pathways leading to cyclobutanes (4) and α-tetralones (5) are also discussed.

CONDENSATION OF PHENOLS AND THEIR DERIVATIVES WITH AROMATIC COMPOUNDS IN THE PRESENCE OF ACIDIC AGENTS. VII. COMPARISON OF THE CONDENSATION OF PHENOLS WITH AROMATIC COMPOUNDS IN HF-SbF5 AND IN THE PRESENCE OF ALUMINUM HALIDES

For the case of a series of phenols of the benzene and naphthalene series it was demonstrated that their condensation processes with benzene and its derivatives in the HF-SbF5 acid system and in the presence of aluminum halides are similar in nature.A possible explanation of the accumulated experimental data on the assumption that the diprotonated forms of the phenols and their ethers or 3, X = Cl, Br> the monoprotonated forms of the oxonium complexes with AlX3 take part in the condensation was considered.

CONDENSATION OF PHENOLS AND THEIR DERIVATIVES WITH AROMATIC COMPOUNDS IN THE PRESENCE OF ACIDIC AGENTS. V. REACTIONS OF CHLORINE-SUBSTITUTED NAPHTHOLS WITH BENZENE

Substitution of the chlorine at position 1 by a phenyl residue occurs readily in the reaction of 1-chloro- and 1,4-dichloro-2-naphthols with benzene in the presence of aluminum chloride and hydrogen chloride. 4-Chloro-2-naphthol reacts with considerably great difficulty, giving a small yield of 4-phenyl-2-naphthol.The possibility of using a mixture of 4- and 2-chloro-1-naphthols for the production of 3-phenyl-1-naphthol was demonstrated.The possible reaction paths are discussed.