Abstract
In this paper we present study concerning the structure, the stability and the reactivity of some new diazinium ylides. Pyrimidinium- and pyridazinium carbalkoxy methylides prove to be stable compounds with the exception of 3-(p-chlorophenyl)pyridazinium carbethoxymethylide 12 which traps athmospheric CO2 leading to a ylide-betaine. A selective way to increase the yield of ylide or betaine has been found. An interesting correlation between structure, stability and reactivity has been found. The structure of ylides and betaine has been proven through elemental and spectral (IR, NMR, MS) analysis as well as by chemical methods. Thus, the ability of diazinium carbalkoxy methylides to react with symmetrical substituted activated alkynes (DMAD) has been studied. Nine new compounds derived from diazines have been obtained.
Highlights
In previous research work we presented a detailed study concerning the syntheses, structure, stability and reactivity of some new 3-p-halophenylpyridazine salts and ylides[8,9] and 4methylpyrimidine salts and ylides.[10]
Continuing our research in this field we decide to change the substituents of the ylide carbanion with carbalkoxy groups and, to see the influence concerning the synthesis, structure, stability, reactivity and properties in the diazinium ylides series
N- carbalkoxy diazinium salts 4-9 were prepared by treating diazines with methyl and ethyl bromoacetate.[12]
Summary
As we show in some recent papers,[1,2,3] the chemistry of cycloimmonium ylides has been widely discussed.[4,5,6,7] In previous research work we presented a detailed study concerning the syntheses, structure, stability and reactivity of some new 3-p-halophenylpyridazine salts and ylides[8,9] and 4methylpyrimidine salts and ylides.[10]. In this case, a part of ylide 13 are trapping atmospheric CO2, leading to betaine 16, Scheme 3. The structure of the new compounds, ylides and betaine, has been proven through elemental (N%) and spectral (IR, 1H-NMR, MS) analysis as well as by chemical methods.
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