Green synthesis of nitrocyclopropane-type precursors of inhibitors for the maturation of fruits and vegetables via domino reactions of diazoalkanes with 2-nitroprop-1-ene / Agnieszka Fryźlewicz, Agnieszka ... więcej

Green synthesis of nitrocyclopropane-type precursors of inhibitors for the maturation of fruits and vegetables via domino reactions of diazoalkanes with 2-nitroprop-1-ene / Agnieszka Fryźlewicz, Agnieszka Kącka-Zych, Oleg M. Demchuk, Barbara Mirosław, Przemysław Woliński, Radomir Jasiński // Journal of Cleaner Production [Dokument elektroniczny]. – 2021, Vol. 292, Spec. Iss., 16 s. : rys., schem., tab., wykr. – Tryb dostępu: https://www.sciencedirect.com/science/article/abs/pii/S0959652621002997. – Oznaczenie ref./art.: 126079. – Bibliogr. s. 14-16, Abstr. – Special Issue : Progress in Smart and Sustainable Technologies. – doi: 10.1016/j.jclepro.2021.126079. – ISSN 0959-6526

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 ... więcej

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.