Nitro-N-ethylanilines

Transformation products of Centr 1 isolated at PicArsn(Refs 10 11) from stored double-base proplnts included nitro- and nitroso- derivs of Centr and products formed on its cleavage by acids. These included N-ethylaniline which, being very reactive, combined immediately with nitrous acid to form N -nitroso-N-ethylaniline which was present in large amt. This product was removed together with 2-nitro-N-ethylaniline from degradation products by steam distn. Some derivs of Centr 1 isolated from aged proplnts possessed stabilizing props... 

N-Ethylaniline and derivs (cont d) N-nitro-N-ethyl-4-nitroaniline 6 E206 trinitro-N-ethylanilines 6 E206... 

Behaviors of proplnts JP 76 RPL 142 on heating at 65° were oot identical. Although the heating of samples of JP 76 continued for 107 weeks, no blistering or evolution of NOg was observed. On the other hand, samples of RPL 142 became blistered and evolved NO after 93 weeks of heating. While in JP 76, N-nitroso-N-ethylaniline was the major primary transformation product of Centr 1 and 4-nitro-centralite was the minor product, the situation was reversed in RPL 142, where 4 nitrocentralite predominated. Furthermore, the rate at which Centr 1 disappeared from JP 76 was about 5 times as great as that at which it was depleted from RPL 142. This was due to the greater initial amt of Centr in JP 76... 

Numerous individual substances were detected only in Ru04 extracts e.g. di- to pentachlorinated benzenes, 4-chlorobenzoic acid and 2,4-dichlorobenzoic acid 24, hexachlorocyclohexanes (a-,P-,y- and 5-HCH) 22, a technical mixture obtained during the synthesis of lindane, and the plasticizers alkylsulfonic acid phenylesters 23. These plasticizers were recently identified in riverine sediments (Franke et al. 1998). Furthermore, nitro-substituted benzoic acid and alkylated phenols 24 were observed. The occurrence of aromatic nitro compounds as a result of the oxidation of anilines can be excluded due to the contemporary appearance of amino compounds, e.g. 4-aminobenzoic acid or N-ethylaniline. However, the origin as well as the emission pathway of these compounds is still unknown. 

N-E< see 4-Chloro-2-nitro-J7-ethylaniline. V-Di-Et 4-chloro-2-nitro-17-dietbylaniline. CioHisO,N,C1. MW, 228-5. Red needles. M.p. 32° ... 

Photodecomposition of some ortfeo-substituted aryldiazonium ions leads to unusual reaction products due to hydrogen atom transfer between the ortho-substituent and the radical center derived by loss of nitrogen from the diazonium ion. Thus, 2-diethylaminobenzenediazonium salts yield N-ethylaniline via the intermediate 3. Deuterium is not incorporated into the benzene ring from either DjO or CD3OD.2 Decomposition of the diazonium salt 4 leads to a benzocyclobutene as the principal product. The influence of the nitro substituent is important, because the un-nitrated diazonium salt is decomposed to give a phenol in the normal manner. ... 

---