Anisole nitro

First of all, there are the two products of O-coupling addition of methoxide ion to the diazonium ion, the (Z)- and (jE)-diazo methyl ethers. As discussed in Section 6.2, they are formed in reversible reactions with half-lives of the order of a fraction of a second (Z) to a minute (E). The two diazo ethers are, however, decomposed rapidly to the final dediazoniation products. We show in Scheme 8-47 the products obtained by Broxton and McLeish (1983 b) in the dediazoniation of 4-chloro-3-nitrobenzenedi-azonium ion (8.64) with methoxide ion in CH3OH. The products are 4-chloro-3-nitro-anisole (8.65, 49 9o), 2-chloro-nitrobenzene (8.66, 449o), and 2-nitroanisole (8.67). 

Nitro-anisol 4-Nitro-toluol 4-Brom-1 -nitro-benzol 1,3-Dinitro-benzol 1-Nitro-naphthalin... 

A New Improved Synthesis of Tricycle Thienobenzazepines Apphcation of chemistry recently developed by Knochel" combined with the well-described halogen dance (HD) reaction, allowed preparation of our key intermediate A in only three synthetic transformations (Scheme 6.4). In this respect, treatment of 2-bromo-5-methylthiophene with hthium diisopropylamide followed by dimethylformamide afforded aldehyde 11 in good yield, lodo-magnesium exchange with conunercial 4-iodo-3-nitro anisole followed by reaction with 11 afforded the thiophene catbinol 12. Dehydroxylation of 12 provided our key intermediate A which presented the requisite functionality to examine our approach to the construction of the seven-member ring system. 

Alkaline reduction of o-nitro-anisole leads (as in the case of nitrobenzene) to the hydrazo-compound, which undergoes a benzidine trans-... 

Trautman, T.D., Ph. D. dissertation "Disposition of p-Nitro-anisole in Mice Mus musculus for Assessment of Hepatic Monooxygenase Capability", Univ. of California, Davis (1978)... 

Substituted nitrobenzenes gave similar results on reduction of less than stoichiometric quantities in the absence of added alkali, hydrogen atom-substrate ratios of 3.0 to 4.1 being obtained while cessation of hydrogen absorption occurred at H/Co = 2.0 in all cases. Azoxy and azo compounds were isolated from o-nitrotoluene (H/substrate = 3.9) p-nitrotoluene (H/substrate = 3.2) yielded a mixture of azoxy and hydroxylamine derivatives, the latter believed to be the immediate precursor of the bimolecular product. Reduction of o-nitro-anisole in the presence of added alkali (NaOH, 3.3X cobalt concentration)... 

Chloro 6 nitro aniline propaquizafop 3 Chloro 6 nitro anisole chlomethoxyfen... 

According to Hojendahl the nitro-anisoles also exhibit very marked deviations from rule III, which may be explained in the same way. 

If we then consider the nitrophenols and nitro-anisoles we find that they behave in an entirely different way. To begin with, the absorption band of anisole is shown in fig. 2. Here the rise of the first benzene band is as steep as in benzene itself and as in the chloro-... 

All of these effects are observed when comparing the rates of various electrophilic aromatic substitution reactions. Activating substituents increase the rate of reaction relative to benzene. The rate of reaction for the nitration of anisole, for example, was 9.7 x 10 times faster than nitration of benzene. The reaction of anisole with nitric and sulfuric acids, gave 44% of o-nitroanisole, 56% of p-nitroanisole and < 1% of m-nitro-anisole.2 9 contrasts with reactions involving deactivating substituents, where selectivity for the meta -product is usually very good. Nitration of nitrobenzene, for example, gave 1,3-dinitrobenzene in 94% yield, with only 6% of the ortho product and < 1% of the para product. ... 

Fig. 3. Separation of an o-, m-, p-mixture of nitro-anisole by a clathrate chromatography system using a Wemer-type compound (elution curve)...

This reaction is assumed to take place via an initial ipso attack of nitro at the iodo position and the subsequent liberation of iodine, which then halogenates at the intermediate to form 2-iodo-4-nitro-anisole and 2,4-diiodoanisole, the latter is then slowly nitrosodeiodinated. ... 

The effect of a hydroxyl or an alkoxyl group on the ease of alkylation is complex. In some instances, the effect appears to be an activation. For example, although nitrobenzene has not been alkylated, o-nitro-anisole has been converted into the isopropyl derivative in good 3ueld. 

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