Secondary amines addition

Nitrenes have a short lifetime (only several microseconds)86- 8 and undergo stabilization by the following reactions isomerization to imines, dimerization to azo compounds, hydrogen abstraction followed by ring closure to heterocyclic compounds, bimolecular insertion into C-H bonds to secondary amines, addition to solvent yielding ylids, and addition to unsaturated systems yielding heterocyclic compounds. Table 117-106 includes the reaction products and references for the different classes of nitrenes. 

Addition of amino-reduc-tones prepared from hex-oses and secondary amines Addition of mixture of glucose and Gly, more effective than either Addition of 0.02% MRP from glucose-Gly Wheat gliadin and hen s egg albumin Over cooking... 

All reactions are reversible and proceed at high temperatures and pressures. In fact the reactions run a multistep course with formation of a range of by-products, particularly dialkyl (secondary) amines. Addition of ammonia in the last stage would suppress the formation of secondary amines. 

Yang, D., and B.R. Mattes. 2002. Polyaniline emeraldine base in N-methyl-2-pyrrolidinone containing secondary amine additives A rheological investigation of solutions. / Polym Sci B Polym... 

D. Yang, G. Zuccarello, B. R. Mattes, Physical stabilization or chemical degradation of concentrated solutions of polyaniline emeraldine base containing secondary amine additives, Macromolecules 2002, 35, 5304. 

Six- and seven-membered cyclic amines and amides, such as pyrrolidinone and morpholine, could be utilized in addition to other secondary amines. Additionally, thiophene and thiophene derivatives could also be C2-aminated using pyrrolidinone (eq 23). 

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