1- Methyl-8-nitronaphthalene

Davies and Warren" found that when 1,4-dimethylnaphthalene was treated with nitric acid in acetic anhydride, and the mixture was quenched after 34 hr, a pale yellow solid with an ultraviolet spectrum similar to that of a-nitro-naphthalene was produced. However, if the mixture was allowed to stand for 5 days, the product was i-methyl-4 nitromethylnaphthalene, in agreement with earlier findings. Davies and Warren suggested that the intermediate was 1,4-dimethyl-5 nitronaphthalene, which underwent acid catalysed rearrangement to the final product. Robinson pointed out that this is improbable, and suggested an alternative structure (iv) for the intermediate, together with a scheme for its formation from an adduct (ill) (analogous to l above) and its subsequent decomposition to the observed product. 

The transformation of arenes in the troposphere has been discussed in detail (Arey 1998). Their destruction can be mediated by reaction with hydroxyl radicals, and from naphthalene a wide range of compounds is produced, including 1- and 2-naphthols, 2-formylcinnamaldehyde, phthalic anhydride, and with less certainty 1,4-naphthoquinone and 2,3-epoxynaphthoquinone. Both 1- and 2-nitronaphthalene were formed through the intervention of NO2 (Bunce et al. 1997). Attention has also been directed to the composition of secondary organic aerosols from the photooxidation of monocyclic aromatic hydrocarbons in the presence of NO (Eorstner et al. 1997) the main products from a range of alkylated aromatics were 2,5-furandione and the 3-methyl and 3-ethyl congeners. 

In the presence of KOH, /m(benzotriazol-l-yl)methane 729 reacts with nitrobenzenes to produce />-(/fc (bcnzo-triazol-lyl)methyl]nitrobenzenes 730 (Scheme 114) <1996TL347>. This vicarious nucleophilic substitution of hydrogen <1991S103> can be considered as a convenient way to />-nitrobenzaldehydes 731. Meta and para substituted nitrobenzenes do not react with compound 729 under these conditions, probably due to steric reasons, but 1-nitronaphthalene reacts producing a naphthalene analog of derivative 730. 

The effect of solvent polarity on the injection conditions for the determination of nitro-PAH by capillary GC with splitless injection was investigated LOD was 129 pg of 2-methyl- 1-nitronaphthalene (228), at SNR 2, RSD 1.8-6.7% when measuring by peak area using FID474. 

A different mode of reaction, however, is observed in photoreductions of nitroaromatics by aromatic tertiary amines. Irradiation of benzene solutions of N-methylated anilines and either m-chloronitrobenzene or 1-nitronaphthalene results in oxidative demethylation of the amines accompanied with reduction of the nitro compound to the corresponding arylamine 49). The authors suggest that hydrogen abstraction from the methyl group takes place as the primary chemical event. 

The wide range of mutagenicities of the methylni-tronaphthalene isomers, e.g., from none detected for 2-methyl-3-nitronaphthalene to 1700 rev/nmol for 2-methyl-6-nitronaphthalene, and the greater activity of 2-nitro- vs 1-nitronaphthalene (Table 10.18), is consistent with the proposal of Yu and co-workers (1992)... 

From Eaborn el al. (1968). Nomenclature e.g., 1M5NN = l-methyl-5-nitronaphthalene. 

Arey, J., R. Atkinson, S. M. Aschmann, and D. Schuetzle, Experimental Investigation of the Atmospheric Chemistry of 2-Methyl-1-nitronaphthalene and a Comparison of Predicted Nitroarene Concentrations with Ambient Air Data, Polycyclic Aromat. Compd., 1, 33-50 (1990). 

Methyl-8-nitronaphthalene-l-sulfonyl chloride, 3385b 1 -Methyl-3-nitro-1 -nitrosoguanidine, 0872... 

Arey, J., Atkinson, R., Aschmann, S.M., Schuetzle, D. (1990) Experimental investigation of the atmospheric chemistry of 2-methyl-1-nitronaphthalene and a comparison of predicted nitroarene concentrations with ambient air data. In Polycyclic Aromatic Compounds. Vol. 1(1-2), pp. 33-50. Gordon and Breach Science Publishers, United Kingdom. 

The most extensive work on the subject so far has been carried out by Brink and Shrieve [44]. The highest yield of 2-methyl-1-nitronaphthalene they obtained was 57% of the theoretical. This was produced by nitrating 2-methylnaphthalene at low temperatures (0-30°C) with a 70% excess of 70% nitric acid The other isomers appeared as a by-product oil. When using a 15% excess of a nitrating mixture composed of 25% HNOs, 55% H2S04 and 20% H20 the yield of 1-nitro-2-methylnaphthalene was also 57%. Dinitration took place when acetic anhydride was used. The product was in the form of a solid with m. p. 209-213°C. No determination of the structure of the dinitroproducts was carried out. 

Some attack para to N02 also observed in some cases, with or without diplacement of X [18], The 1-position is attacked even in the case of, for example, 1 -methyl-2-nitronaphthalene [19]. 

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