- N-Nitroso- and N-Nitrotrialkylureas and Their Decomposition
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The synthesis and decomposition of N-(n-butyl)-N',N'-dimethyl-N-nitrosourea (2a), N-(n-butyl)-N',N'-dimethyl-N-nitrourea (3a), N',N'-dimethyl N-(1-norbornyl)-N-nitrosourea (2b), N',N'-dimethyl-N-(1-norbornyl)-N-nitrourea (3b) are described.Several of the compounds show complex NMR spectra ascribable to rotational isomerism.Decomposition of 2a and 3a gave n-butyl N,N-dimethylcarbamate and tetramethylurea, while decompostion of 2b and 3b in methylene chloride gave 1-norbornyl N,N-dimethylcarbamate and 1-norbornyl chloride.These products are formed via diazotic acid derivatives and carbonium ion pairs; the reaction mechanism is essentially the same as that established for the closely related N-nitrosoamides.In concentrated solutions, nitrosourea 2a yielded a new product, amino acid 20.
- White, Emil H.,Ryan, Thomas J.,Hahn, Bo Sup,Erickson, Ronald H.
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p. 4860 - 4866
(2007/10/02)
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- REACTION OF ORGANIC CARBONATES WITH AMINES. II. REACTION OF ALKYL PHENYL CARBONATES WITH SECONDARY AMINES
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The reaction of alkyl phenyl carbonates with secondary amines leads to the formation of N,N-dialkylurethanes and phenols.The reaction has overall second order.The effect of the substituents in the aromatic ring of the alkyl phenyl carbonates and the polarity of the solvent on the reaction rate was investigated.
- Mikheev, V. V.,Svetlakov, N. V.,Garipov, R. M.,Kalmykova, N. D.
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p. 1865 - 1868
(2007/10/02)
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