16620-67-0Relevant academic research and scientific papers
Intramolecular Conversion of N-Nitroso Ketimines into Ketones and Nitrogen. 1,2,3-Oxadiazetines as Analogues of Dioxetanes
White, Emil H.,Wilson, Alan A.,Anhalt, John P.,Baumgarten, Ronald J.,Choca, Jose I.
, p. 2892 - 2896 (1982)
N-Nitrosobenzophenone imine and N-nitrosocamphorimine have been prepared by the nitrosation of the corresponding imines with nitrosyl chloride or dinitrogen tetraoxide.N-Nitrosobenzophenone imine decomposes by first-order kinetics to yield benzophenone and nitrogen; the activation parameters are ΔH25(excit.) = 18.7 kcal/mol and ΔS25(excit.) = -11 eu.The reaction is not affected appreciably by small amounts of water, and the use of H2(18)O has shown that the oxygen atom of the nitroso imine is retained in the benzophenone.The kinetic information, entropy ofactivation, and lack of water incorporation indicate that the ketone-forming reaction is an intramolecular one.A proposed intermediate in this decomposition bears a resemblance to the dioxetanes, which are known to yield excited states on decomposition.However, we were unable to detect excited states from the decomposition of either N-nitrosobenzophenone imine or the nitroso imine of N-methylacridone.
Kinetics and mechanism of the thermal decomposition of N-nitrosodiphenylmethylimine
Liu, Michael T. H.,Ibata, Toshikazu
, p. 559 - 562 (2007/10/02)
The thermal decomposition of N-nitrosodiphenylmethylimine has been investigated in various solvents.The decomposition products are benzophenone and nitrogen.The ΔH(act.) and ΔS(act.) parameters for these first-order decompositions have been determined.The experimental evidence is consistent with the hypothesis that the thermolysis of N-nitrosodiphenylmethylimine involves the formation of a cyclic transition state via an electrocyclic ring closure mechanism.
