On the basis of the results of IR and UV spectroscopy, a considerable decrease in the efficacy of the conjugation of the unshared pair of the nitrogen atom with a carbonyl group in ynaziridines as compared with ynamines has been shown.The difference in the electronic structures of these compounds finds its reflection in their chemical behavior: the electrophilicity of the triple bond in an ynaziridine is higher than that in the analogous ynamine in reaction with amines.
Shubina, Yu. V.,Tikhomirov, D. A.,Eremeev, A. V.
p. 516 - 520
(2007/10/02)
YNAZIRIDINES. METHODS OF SYNTHESIS OF A NEW TYPE OF YNAMINES
Ways of synthesizing ynaziridines by succesive halogenation and dehydrohalogenation of enaziridino esters, the reaction of potassium aziridinide with bromophenylacetylene, the reaction of 1H-aziridines with the methyl ester of bromopropionic acid was studied.The different direction of the reaction of aziridines with bromomethylpropiolate as a function of the nature of the solvent was demonstrated.In methanol the addition of aziridine to the triple bond proceeds stereospecifically with the formation of the E-isomer.When this reaction was conducted in ether, ynaziridines were obtained for the first time.An effective method of synthesis of ynaminoesters was developed.
Tikhomirov, D. A.,Shubina, Yu. V.,Eremeev, A. V.
p. 1231 - 1235
(2007/10/02)
Synthesis of 1-Methoxycarbonylethynylaziridines and Methoxycarbonylynamines
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Tikhomirov, D. A.,Shubina, Yu. V.,Eremeev, A. V.
p. 1138
(2007/10/02)
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