Abstract
The “green” and selective methodology for the preparation of precursors of cyclopropene-type inhibitors for the maturation of fruits or vegetables was described. It was found out that 2-nitroprop-1-ene undergoing reactions with diaryldiazomethanes under mild conditions yields 3,3-diphenyl-5-methyl-5-nitro-Δ1-pyrazolines. Under the applied conditions the primary reaction products are spontaneously transformed via nitrogen extrusion to form respective 1,1-diaryl-2-methyl-2-nitrocyclopropanes. All synthetized compounds were fully characterized by spectral methods and structural roentgenography (X-ray). The reaction course was explored in detail at molecular scale using advanced quantumchemical calculations. A Bonding Evolution Theory (BET) study along with the [3 + 2] cycloaddition (32CA) reaction of the 2-nitroprop-1-ene with diphenyldiazomethane as well as nitrogen elimination from 3,3-diphenyl-5-methyl-5-nitro-Δ1-pyrazoline allows an explanation of the molecular mechanism. As a consequence the programming of a wide range of synthesis of similar compounds will be possible.
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