Green, one-pot synthesis of 1,2-oxazine-type herbicides via non-catalyzed Hetero Diels-Alder reactions comprising (2E)-3-aryl-2-nitroprop-2-enenitriles

The First Examples of [3+2] Cycloadditions with the Participation of (E)-3,3,3-Tribromo-1-Nitroprop-1-Ene

“…For this purpose, the data obtained from the DFT wb97xd/6-311+G(d) (PCM) computational study was applied ( Table 2 and Table 3 ). For the resolving of mechanistic aspects of different-type pseudocyclic organic reactions, a similar level of the theory was used [ 28 , 29 , 30 ]. The DFT calculations for the model cycloaddition 1c+2 shows that the enthalpy and Gibbs free energy factors are favoring the formation of 3,4-cis-3,4-trans cycloadduct, which was isolated from the postreaction mixture.…”

Fully Selective Synthesis of Spirocyclic-1,2-oxazine N-Oxides via Non-Catalysed Hetero Diels-Alder Reactions with the Participation of Cyanofunctionalysed Conjugated Nitroalkenes

“…Firstly we decided to shed light on the nature of global and local interactions between cycloaddition components. We analysed the electronic properties of E-2-aryl-1-cyano-1-nitroethenes in the Conceptual Density Functional Theory (CDFT) framework within our previous works [ 35 ]. It was found that all of these-type compounds exhibit an electrophilic nature.…”

“…For this purpose, the ωB97X-D/6-311G-(d) level of theory was applied. The similar approach we used previously for the discussion of mechanistic aspects of many bimolecular reactions, such as DA processes [ 45 ], [3 + 2] cycloadditions [ 46 ], [4 + 3] cycloaddition [ 47 ] and many other [ 35 , 48 ].…”

Full Regio- and Stereoselective Protocol for the Synthesis of New Nicotinoids via Cycloaddition Processes with the Participation of Trans-Substituted Nitroethenes: Comprehensive Experimental and MEDT Study

“…To provide a quantitative view of reactivity in terms of classical concepts, such as nucleophilicity and electrophilicity, the Conceptual Density Functional Theory (CDFT) [16][17][18] indices were calculated. The global reactivity indices have been proven to be a powerful tool to describe the reactivity in many studies of polar reactions [19][20][21][22][23] The calculated values for 1-nitropropene 2c, its halogenated derivatives 2a and 2b, and nitrone 1 are gathered in Table 1. The electronic chemical potential µ of 1-nitropropenes 2a-c exhibits a much lower value than the nitrone 1, from −5.00 eV to −5.74 eV and −3.65 eV, respectively, indicating that, in a polar process, the electron density transfer will take place from the nitrone 1 to 1-nitropropenes.…”