Unexpected course of reaction between (E)-2-aryl-1-cyano-1-nitroethenes and diazafluorene: why is there no 1,3-dipolar cycloaddition?
نویسندگان
چکیده
ABSTRACT Reactions between (E)-2-aryl-1-cyano-1-nitroethenes and diazafluorene lead to acyclic 2,3-diazabuta-1,3-diene derivatives, instead of the expected pyrazoline systems. DFT calculations suggest that this is a consequence of formation of zwitterionic structure in the first stage of the reaction. It must be noted that this is a specific property of the (E)-2-aryl-1-cyano-1-nitroethenes group, in contrast to most other conjugated nitroalkenes. GRAPHICAL ABSTRACT
منابع مشابه
Kinetics of the [4+2] cycloaddition of cyclopentadiene with (E)-2-aryl-1-cyano-1-nitroethenes
ABSTRACT The electrophilicity of (E)-2-aryl-1-cyano-1-nitroethenes is not sufficient to induce a zwitterionic course of their [4+2] cycloaddition to cyclopentadiene. The one-step mechanism of these reactions is indicated by the activation parameters, and the substituent and solvent effects on the reaction. GRAPHICAL ABSTRACT
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عنوان ژورنال:
دوره 148 شماره
صفحات -
تاریخ انتشار 2017