Aromatic compounds methoxynaphthalene

A combination of Cp nCX —A CXC) (where = cyclopentadienyl) effectively promotes the Friedel-Crafts coupling of glycosyl fluorides with aromatic compounds, such as trimethoxyben2ene or methoxynaphthalenes. The derived C-aryl glycosides are potent antitumor agents (39). 

Figure 3.1 Acetylation at 373 K with acetic anhydride of a series of aromatic compounds over HBEA-15 zeolite. Conversion (XSUB) of anisole ( ), 2-methoxynaphthalene (x), m-xylene ( ), toluene ( ), 2-methylnaphthalene (o) and fluorobenzene (a) versus time. Reprinted from Journal of Catalysis, Vol. 230, Guidotti et al. Acetylation of aromatic compounds with H-BEA zeolite the influence of the substituents on the reactivity and on the catalyst stability, pp. 375-383, Copyright (2005), with permission from Elsevier...

The anodic methoxylation of aromatic compounds such as naphthalene [41], anthracene [42], alkylbenzenes [31,43], phenols [44-46], anisoles [33,47-54] and other alkoxyben-zenes [53], methoxynaphthalenes [33], methoxyanthracenes [50,54], inden-l-ones [55], / a/r/-substituted anilides [56] and heterocyclic compounds, such as furans [57], thiophenes [58], and pyrroles [59], has received considerable attention. 

D.ii. Addition to Aromatic Derivatives. Aromatic compounds also react with carbenes, but ring expansion usually follows the initial cyclopropanation. In a typical example, 2-methoxynaphthalene (373) reacted with dichlorocarbene to give 374, and subsequent ring expansion gave 375, 99 which is a general reaction of enol ethers, which give either unsaturated acetals or unsaturated carbonyls. oo... 

The production of polysulfones was shown to be possible in Ref [181] by means of interaction of sulfuric acid, suffm trioxide or their mixes with aromatic compounds (naphthalene, methylnaphthalene, methoxynaphthalene, dibenzyl ester, bisphenylcarbonate, bisphenyl, stilbene) if one used the anhydride of carbonic acid at 30-200 °C as the process activator. Obtained polymers could be reprocesses by means of pressing. 

Friedel-Crafts Reactions. Aluminum trifluoromethanesulfonate has been used for the Friedel-Crafts alkylation reaction of toluene with isopropyl and tert-butyl chlorides (eq 1), and for the acylation of benzene and toluene with acetyl and benzoyl chlorides in low to moderate yields. Intramolecular Friedel-Crafts acylation of an aromatic compound with Meldrum s acid has also been reported using catalytic amounts of Al(OTf)3. Acylation of 2-methoxynaphthalene with acetic anhydride has been reported using Al(OTf)3 and lithium perchlorate as an additive to afford the corresponding 6-acetylated adduct in 83% yield. Effective acylation of arenes with carboxylic acids has also been disclosed using polystyrene-supported Al(OTf)3. ... 

A kinetic study9 of the mechanism of acid-catalysed chlorination of a range of substituted phenols by A-chlorobenzenesulfonamide has suggested a common mechanism for the compounds studied, with a change in rate-limiting step with the varying nature of the substituents. The formation of some novel addition products on bromination of some bicyclic aromatics has been reported.10 Bromination of 1-methoxynaphthalene... 

In an attempt to obtain further evidence of the mechanism, the behavior of 2-methoxynaphthalene and 2-trimethylsiloxynaphthalene under standard conditions was studied. Neither compound would be expected to take part in an ene reaction, nor involve a Lewis acid-stabilized transition state, and if a reaction did occur, it would suggest a conventional electrophilic aromatic substitution. However, neither compound showed any reaction with DEAD in the presence of LiC104 at room temperature for some... 

Instead of dienes, aromatic substrates can also participate in tandem cyclopropanation/Cope rearrangement sequences893 894. Rhodium(II) trifluoroacetate catalyzed decomposition of 17 affords the unstable bicyclo[3.2.2] compound 149 in 29% yield893. The reactions of anisol and 1-methoxynaphthalene with 17 show that in the case of electron-rich aromatics side reactions (alkylation reactions) can compete with cyclopropanation reactions due to dipolar intermediates and products 150 and 151, respectively, are formed893. 

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