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

Fryźlewicz, Agnieszka; Kącka‐Zych, Agnieszka; Demchuk, Oleg M.; Mirosław, Barbara; Woliński, Przemysław; Jasiński, Radomir

doi:10.1016/j.jclepro.2021.126079

Cited by 16 publications

(13 citation statements)

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“…For comparison, the C3–O4 interatomic distance at this level is longer than 3.8 Å. This distance exists beyond the typical range for this type of bonds; within transition states 44,50,51 TS1a exhibits evidently polar nature. This is confirmed by the high GEDT value (0.61 e).…”

Section: Resultsmentioning

confidence: 79%

“…This process does not require overcoming of the activation barrier and is connected with the reduction of the reaction system enthalpy of about 8 kcal/mol (Table 2). The MCa does not exhibit the nature of electron density transfer complex 44 . Pre‐reaction complexes of similar type have been detected very recently regarding some examples of different types of polar cycloaddition reactions 27,47–49 …”

Section: Resultsmentioning

confidence: 94%

“…The ELF molecular geometries and basin attractor positions were visualized using the GaussView program 39 . A similar approach was successfully used to explain the mechanism of different types of reactions 17,40–44 …”

Section: Computational Proceduresmentioning

confidence: 99%

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Mechanistic aspects of the synthesis of seven‐membered internal nitronates via stepwise [4 + 3] cycloaddition involving conjugated nitroalkenes: Molecular Electron Density Theory computational study

Kącka‐Zych

Jasiński

2022

J Comput Chem

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The density functional theory computational study indicates the possibility of the synthesis of seven-membered internal nitronates via cycloaddition reactions involving Z-C-aryl-N-methylnitrones and E-2-aryl-1-cyano-1-nitroethenes. The detailed exploration of the reaction paths indicates a polar, stepwise reaction mechanism through the zwitterionic intermediate. Using bonding evolution theory (BET), we have deciphered the molecular mechanism of the [4 + 3] cycloaddition reaction between E-2-phenyl-1-cyano-1-nitroethene and Z-C-phenyl-N-methylnitrone. The BET study has revealed that the formation of two C O single bonds takes place in the same way, through the depopulation of N C and C C bonding regions and monosynaptic basins, respectively. The first O1 C7 single bond was formed in the sixth phase, while the second C3 O4 bond was formed in the last ninth phase.

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Section: Resultsmentioning

confidence: 79%

Section: Resultsmentioning

confidence: 94%

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Mechanistic aspects of the synthesis of seven‐membered internal nitronates via stepwise [4 + 3] cycloaddition involving conjugated nitroalkenes: Molecular Electron Density Theory computational study

Kącka‐Zych

Jasiński

2022

J Comput Chem

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“…In particular, for both MCA and MCB, the C3–C4 distances were 3.82 Å, whereas the C5-O1 distances were about 2.7 Å. Thus, the interatomic distances were beyond the typical range for the corresponding distances at transition states [ 36 , 37 , 38 , 39 , 40 ]. It should be underlined that these MC s did not exhibit the nature of electron density transfer complexes [ 41 ].…”

Section: Resultsmentioning

confidence: 97%

“…This analysis was performed based on CDFT reactivity indices ( Table 1 ) [ 34 ]. A similar approach was recently used to explain the course of many different types of cycloaddition processes [ 35 , 36 , 37 , 38 ]. It was found that nitrones 1 exhibited a moderately electrophilic nature.…”

Section: Resultsmentioning

confidence: 99%

On the Question of Zwitterionic Intermediates in the [3 + 2] Cycloaddition Reactions between C-arylnitrones and Perfluoro 2-Methylpent-2-ene

et al. 2021

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The molecular mechanism of the [3 + 2] cycloaddition reaction between C-arylnitrones and perfluoro 2-methylpent-2-ene was explored on the basis of DFT calculations. It was found that despite the polar nature of the intermolecular interactions, as well as the presence of fluorine atoms near the reaction centers, all reactions considered cycloaddition proceed via a one-step mechanism. All attempts for the localization of zwitterionic intermediates on the reaction paths were not successful. Similar results were obtained regardless of the level of theory applied.

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Lean 4.0 in the value co‐creation in agro‐industrial services: An agenda for future studies for the efficient resource use

et al. 2023

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Over the last few years, the Lean 4.0 concept has emerged and gained prominence on the world stage for waste and efficient natural resources management, once including the Lean thinking philosophy for management and technologies from Industry 4.0 for supporting and sharing data and information among the actors in the supply chain. This new management technic allows reorganizes the business process and stimulates the circular supply chain based on intelligent services and sharing data, information and know‐how among the actors in production systems. However, it is not clear in the current literature that the opportunities are linked to the relationship between Lean 4.0 and the efficient use of resources in the agro‐industrial environment. Based on the exposure, this paper intends to show an agenda for future research linked to Lean 4.0 in the value co‐creation in agro‐industrial services. We identified five topics for future research that are related to Lean 4.0 for efficient resource use.

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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

Cited by 16 publications

References 61 publications

Mechanistic aspects of the synthesis of seven‐membered internal nitronates via stepwise [4 + 3] cycloaddition involving conjugated nitroalkenes: Molecular Electron Density Theory computational study

Mechanistic aspects of the synthesis of seven‐membered internal nitronates via stepwise [4 + 3] cycloaddition involving conjugated nitroalkenes: Molecular Electron Density Theory computational study

On the Question of Zwitterionic Intermediates in the [3 + 2] Cycloaddition Reactions between C-arylnitrones and Perfluoro 2-Methylpent-2-ene

Lean 4.0 in the value co‐creation in agro‐industrial services: An agenda for future studies for the efficient resource use

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