83785-97-1Relevant academic research and scientific papers
Convenient methodology for the synthesis of trialkylhydrazines
Vazquez, Alvaro J.,Rodriguez, Cristian,Nudelman, N. Sbarbati
scheme or table, p. 3958 - 3972 (2009/12/24)
A convenient methodology, based on the addition of organolithium compounds to N-nitrosamines, was developed for the synthesis of substituted hydrazones and trialkyl hydrazines. The reaction is very sensitive to the reaction conditions, particularly the [R
The reaction of nitrosodicyclohexylamine with organolithiums
Vazquez, Alvaro J.,Rodriguez, Cristian,Nudelman, N. Sbarbati
experimental part, p. 1098 - 1104 (2009/10/26)
The detailed study of the reaction of N-nitrosamines with organolithium compounds, under different reaction conditions, allowed the development of a useful methodology for the synthesis of substituted hydrazones and trialkyl hydrazines. The reaction proved to be very sensitive to the reaction conditions, and different main products can be obtained by ine tuning of several variables. With the purpose of searching into the reaction mechanism, a careful isolation, characterization, and quantitative determination of several minor products was carried out. N,N-dicyclohexylamine, N-cyclohexylidencyclohexyl amine, and N,N,N′-dicydohexylalkylhydrazines, were the main side products identified after the work up of the reaction mixtures. With the same aim, the kinetics of the reaction of N-nitrosodicyclohexylamine with n-BuLi, was determined at temperatures in the range 0°C room temperature. Under the conditions leading to the trialkyl hydrazine, the results show an abrupt slowdown of the reaction rate, after a short reaction time. This result, together with other observations, such as the recovering of hydrazone even when using high [RLi], is indicative of equilibrium involving different species in the reaction mixture. The isolation of reduction products, as well as additional experiments carried out with lithium dialkylamides and NO, allowed suggestion of an overall mechanistic scheme for the complex consecutive and parallel reactions, that is consistent with the afforded evidences. Copyright
