99647-87-7

Upstream product

• 53380-17-9 4,4-diphenyl-valeric acid 
• 10240-08-1 4-methyl-1-naphthol 
• 71-43-2 benzene 
• 24821-54-3 1-methoxy-4-methylnaphthalene 
• 35959-54-7 4-hydroxy-4-phenyl-valeric acid 
• 7210-42-6 5-methyl-5-phenyl-dihydro-furan-2-one 
• 16020-97-6 3,3-diphenylcyclopentanone 

Downstream Products

• 957-26-6 4-methyl-4-phenyl-4H-naphthalen-1-one 
• 145968-48-5 cis-(1R,4R)-4-methyl-4-phenyl-1,2,3,4-tetrahydro-1-naphthol 
• 146075-72-1 trans-(1S,4R)-4-methyl-4-phenyl-1,2,3,4-tetrahydro-1-naphthol 
• 146075-74-3 cis-(1S,4S)-4-methyl-4-phenyl-1,2,3,4-tetrahydro-1-naphthol 
• 33006-06-3 1-Methyl-1-phenyl-1,2-dihydro-naphthalin 

Relevant academic research and scientific papers

Catalytic activation of carbon-carbon bonds in cyclopentanones

In the chemical industry, molecules of interest are based primarily on carbon skeletons. When synthesizing such molecules, the activation of carbon-carbon single bonds (C-C bonds) in simple substrates is strategically important: it offers a way of disconnecting such inert bonds, forming more active linkages (for example, between carbon and a transition metal) and eventually producing more versatile scaffolds. The challenge in achieving such activation is the kinetic inertness of C-C bonds and the relative weakness of newly formed carbon-metal bonds. The most common tactic starts with a three- or four-membered carbon-ring system, in which strain release provides a crucial thermodynamic driving force. However, broadly useful methods that are based on catalytic activation of unstrained C-C bonds have proven elusive, because the cleavage process is much less energetically favourable. Here we report a general approach to the catalytic activation of C-C bonds in simple cyclopentanones and some cyclohexanones. The key to our success is the combination of a rhodium pre-catalyst, an N-heterocyclic carbene ligand and an amino-pyridine co-catalyst. When an aryl group is present in the C3 position of cyclopentanone, the less strained C-C bond can be activated; this is followed by activation of a carbon-hydrogen bond in the aryl group, leading to efficient synthesis of functionalized α-tetralones - a common structural motif and versatile building block in organic synthesis. Furthermore, this method can substantially enhance the efficiency of the enantioselective synthesis of some natural products of terpenoids. Density functional theory calculations reveal a mechanism involving an intriguing rhodium-bridged bicyclic intermediate.

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

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.