851330-27-3

Upstream product

• 637-69-4 4-Methoxystyrene 
• 119842-49-8 1-(1-isocyanovinyl)-4-methoxybenzene 
• 874-90-8 4-methoxybenzonitrile 
• 119842-40-9 N-[1-(4-Methoxy-phenyl)-vinyl]-formamide 
• 768-60-5 4-methoxyphenylacetylen 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 872796-23-1 7-methoxy-1-(4-methoxy-phenyl)-naphthalene-2,3-dicarboxylic acid 
• 87797-13-5 1,2,3,4-tetrahydro-7-methoxy-1-(4'-methoxyphenyl)naphthalene 

Downstream Products

• 87797-13-5 1,2,3,4-tetrahydro-7-methoxy-1-(4'-methoxyphenyl)naphthalene 

Relevant academic research and scientific papers

Electrochemical [4+2] Annulation-Rearrangement-Aromatization of Styrenes: Synthesis of Naphthalene Derivatives

We report the first electrochemical strategy to synthesize functionalized naphthalene derivatives through [4+2] annulation—rearrangement–aromatization from styrenes under mild conditions. The electrolysis does not require metals, oxidants and high valence substrates, indicating the atom and step-economy ideals. The dehydrodimer produced through [4+2] cycloaddition of 4-methoxy α-methyl styrene is isolated and proved to be the key intermediate for the following oxydehydrogenation to form carbon cation, which undergoes rearrangement–aromatization to afford the final products. This reaction represents a powerful access to construct multi-substituted naphthalene blocks in a single step.

Direct Conversion of Nitriles into Alkene “Isonitriles”

The sequenced addition of RLi to nitriles, trapping with isopropylformate, and dehydration with phosphoryl chloride provides an efficient, direct synthesis of alkene isocyanides. The one-pot sequence involves a series of carefully orchestrated steps: addition, formylation, tautomerization, and dehydration, with CuCN catalyzing a key equilibration of a formyl imine to an N-formyl enamine. The resulting aromatic alkeneisocyanides, that are otherwise challenging to synthesize, engage in an unusual [4+2]-type cycloaddition/1,3-H shift/decyanation sequence to afford substituted naphthalenes.

Ruthenium porphyrin bound to a Merrifield resin as heterogeneous catalyst for the cyclooligomerization of arylethynes

Ruthenium meso-tetraphenylporphyrin was bound to a solid support, the Merrifield resin, and used in the cyclooligomerization of arylethynes, obtaining high yields and selectivities in the final products with a complete recycling of the catalyst.

The highly selective formation of biaryls by the cyclization of arylethynes catalyzed by vanadyl phthalocyanine

The dimerization of arylethynes catalyzed by vanadium phthalocyanine to give substituted biaryls has been investigated. The reaction yield is always high and for many examples is only slightly affected by the aryl substituents. This fact is also related to the results obtained with metalloporphyrins, which give lower selectivities due to the presence of variable amounts of triphenylbenzenes.

General synthesis of 8-aryl-2-tetralones

Two alternative routes are described for the synthesis of 8-aryl-2-tetralones (1). Route A starts from α-tetralone 3 and involves 3 or 4 steps, with the selective Na-EtOH reduction of 1-aryl-7-methoxynaphthalenes 2 being the key step. The exclusive reduct

Ring selectivity in the Na/EtOH reduction of 1-aryl-7-methoxynaphthalenes

Na/EtOH reduction of 1-aryl-7-methoxynaphthalenes occurred preferentially at the A-ring when no substituents were present at the ortho-positions of the aryl group (up to 100% selectivity), to afford 1-aryl-7-methoxy-1,2,3,4- tetrahydronaphthalenes. Ortho-

The formation of 1-aryl-substituted naphthalenes by an unusual cyclization of arylethynes catalyzed by ruthenium and rhodium porphyrins

The dimerization of arylethynes to give 1-aryl-substituted naphthalenes through catalysis by rhodium and ruthenium porphyrins has been investigated. When performed at temperatures above 130 °C, this reaction affords a mixture of triarylbenzenes and 1-aryl-substituted naphthalenes. The yields of naphthalene derivatives range from low to high, depending on the temperature and the phenyl substituents. The concentrations of the initial compounds affect the selectivity of the reaction: the dimerization/trimerization ratios in 1,2-dichlorobenzene increase as concentration decreases. The reaction mechanism is determined by the peculiar structure of the catalyst ligand and involves the formation of a vinylidene intermediate of the metalloporphyrins. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.