N-Nitroso-amines

Nitrosation of amines is best illustrated by examining what happens when a sec ondary amine reacts with nitrous acid The amine acts as a nucleophile attacking the nitrogen of nitrosyl cation The intermediate that is formed m the first step loses a pro ton to give an N nitroso amine as the isolated product... 

N Nitroso amines are more often called nitrosamines and because many of them are potent carcinogens they have been the object of much investigation We encounter nitrosamines m the environment on a daily basis A few of these all of which are known carcinogens are... 

Secondary alkylamines and secondary arylamines y e d N nitroso amines... 

Nitrosation (Section 22 15) The reaction of a substance usu ally an amine with nitrous acid Pnmary amines yield dia zonium 10ns secondary amines yield N nitroso amines Tertiary aromatic amines undergo nitrosation of their aro matic ring... 

N Nitroso amine (Section 22 15) A compound of the type R2N—N=0 R may be alkyl or aryl groups which may be the same or different N Nitroso amines are formed by ni trosation of secondary amines... 

Further derivatives of amines in which the a-C,H groups are sufficiently acidic to enable metalation are carbamates [235,238-240] (Scheme 5.26), imides[241], N-nitroso amines [59,242], ureas [201,243], some N-phosphorus derivatives [212, 214, 226, 244, 245], N-(2-pyridyl)amines (Scheme 5.26), and isonitriles [59]. A potential side reaction in the examples in Scheme 5.26 is the lithiation of the arene this is, in fact, observed with an isomeric dipyridopyrazine (last reaction, Scheme5.26). 

Tetraaza-tricyclo 7,3,0.04,8l dodec-2-en 2-oxid E16a, 1236 (aus N-Nitroso-amin)... 

DieReduktion der Nitrone, Hydroxylamine, N-Nitroso-amine usw. istz.Tl. praparativ ohne Bedeutung und bereits an anderen Stellen ds. Handb. abgehandelt. 

Nitrosamines - N-Nitroso amines compounds of the structure R NNO. Compounds RNHNO are not ordinarily isolatable, but they, too, are nitrosamines. The name is a contraction of N-nitrosoamine and, as such, does not require the N locant. 

In contrast to the authors (Hovinen et al., 1992) of this scheme, we represent the equilibrium Kq between the diazenol and the N-nitroso amine with dotted rather than full arrows, because it is likely that it is not an intramolecular proton rearrangement (see Reynolds and Thomson, 1986). We label the rate constant for the NO-bond heterolysis of the diazenol with k. This is consistent with the later papers of Fishbein s group, discussed below. 

This product is called an N-nitroso amine. For short, chemists often call it a nitrosamine. 

Nucleophilic substitution reactions that occur under conditions of amine diazotization often differ significantly in stereochemistry, as compared with that seen in halide or arenesulfonate solvolysis. Diazotization occurs via an N-nitroso amine which decomposes to a carbonium ion, molecular nitrogen, and water ... 

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