N-Nitrosoamines

N-Nilrosoamines are reduced easily lo ihe hydrazine and, if continued, lo the amine (62). Early workers ruled out cleavage of dimeihylhydrazine as the source of dimethylamine in hydrogenation of N-nitrosodimethylamine since liule ammonia was found the letramethylietrazene was implicated in the hydrogenolysis (fSI). Palladium-on-carbon under mild conditions is used for industrial production of dialkyl hydrazines from N-nitrosoamines. 

In Sections 3.1 to 3.3 the discussion of the mechanism of diazotization concentrated on the rate-determining part of the reaction which, in most cases, does not include steps occurring after the formation of the A-nitrosoamine. The various pathways of nitrosation are summarized in Scheme 3-35. The transformation of the N-nitrosoamine will be discussed in Section 3.4. 

It is worth noting, however, that the prototropic equilibrium between the N-nitrosoamine (3.7) and the diazohydroxide (3.9) has been determined semiquan-titatively for the analogous diazotization of an aliphatic amine. Fishbein and coworkers (Hovinen et al., 1992) determined an upper limit for the nitrosoamine equilibrium concentration (<1.5% see also Zollinger, 1995, Sec. 7.2). 

The initial product is a salt of hydrazinesulfonic acid, which is converted to the hydrazine by acid treatment. Diazonium salts can also be reduced to arenes (14-24). N-Nitrosoamines can be denitrosated to secondary amines by a number of reducing agents, including H2 and a catalyst, BF3—THF—NaHC03, and NaBH4— TiCU, as well as by hydrolysis. ... 

Very little information is available on the uptake of N-nitrosoamine from soils by plants. Uptake of W-nitrosodimethyl-amine and N-nitrosodiethyl amine from soil by wheat, barley and... 

W-nitrosodiethylamine from soil by wheat, barley and several vegetable crops has been demonstrated (17,18). Rapid disappearance of the N-nitrosoamine absorbed by plants was observed. Sander et al. (19) observed that several W-nitrosoamines could be removed from water by cress, but the residues rapidly decreased when W-nitrosamine containing water was replaced with non-contaminated water. Dean-Raymond and Alexander (20) reported... 

N-nitrosoamines cannot be dissected into active and inactive regions, but they must be considered in their entirety. Therefore, one cannot simply look at the compounds and predict their carcinogenicity because no single region of the structure is responsible for the biological activity [81]. 

N-Hydroxy-N-nitrosoamines also known as nitrosoalkoxyamine belong to the class of C-diazeniumdiolate compounds. Several protocols have been used in the past to name compounds containing the diazeniumdiolate functional group. This has not... 

Nitrogen species, such as nitrate and nitrite, are known to be confirmed procarcinogens. The excessive input of these nitrogen compounds with food and drinking water in the presence of tertiary amines, for instance, from medicines, can lead to the formation of carcinogenic N-nitrosoamines. 

N-nitosoamine Reduction The reduction of N-nitrosoamines can occur across either the N-N bond or the N-0 bond. Both reactions ultimately result in the formation of the parent amine and ammonia. 

M. Zheng, C. Fu and H. Xu, High-performance liquid chromatographic detection of trace N-nitrosoamines by precolumn derivatization with 4-(2-phthalimidyl)benzoyl chloride. Analyst, 1993,118(3), 269-271. 

Certain aromatic nitroso compounds can be obtained in good yields by irradiation of the corresponding nitro compounds in 0.1 M aqueous KCN with uv light.592 The reaction has also been performed electrochemically.593 When nitro compounds are treated with most reducing agents, nitroso compounds are either not formed or react further under the reaction conditions and cannot be isolated. N-Nitroamines have been reduced to N-nitrosoamines with Bu3SnH-azobisisobutyrylnitrile.594... 

Direct amination of aromatic rings 1-25 Aminoalkylation of aromatic rings 1-32 Rearrangement of N-nitroamines 1-33 Rearrangement of N-nitrosoamines... 

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