Abstract
In the present work, the formation of the four-membered cyclic nitronates and the retro (3 + 2) cycloaddition (retro-32CA) reaction of the 4H-[1,2]oxazete 2-oxide were studied using the density functional theory method at the MPWB1K/6-311G(d,p) theoretical level. The electronic structure of 3-tert-butyl-4,4-dimethyl-1,2-dinitro-pent-2-ene was known through electron localization function analysis, natural population analysis, and molecular electrostatic potential analysis. The formation of 4,4-di-tert-butyl-3-nitromethyl-4H-[1,2]oxazete 2-oxide proceeds through a one-step mechanism. The mechanism of the retro-32CA leading to di-tert-butyl ketone and nitrile oxide derivative should be described as an asynchronous two-stage one-step process. The bonding evolution theory study was carried out to clarify the mechanisms of the formation of 4H-[1,2]oxazete 2-oxide and their retro-32CA.
Highlights
The Electron Localization Function (ELF) basin attractor positions, together with the most important valence basin populations, the ELF-based Lewis structure, together with the natural atomic charges obtained through the natural population analysis (NPA) analysis and the analysis of the molecelectrostatic potential (MEP) of the substrate, the NPA
The MPWB1K/6-311G(d,p) tionary points involved in the formation of [1,2]oxazete 2-oxide derivative (3a–c) and their calculations indicate that formation of 4,4-di-tert-butyl-3-nitromethyl-4H-[1,2]oxazete 2retro-32CA reaction are collected in Table 1 and Figure 2
We find a transition state (TS2a, d(C1-C2) = 1.927 Å and d(N3-O4) = 2.011 Å) of the retro-32CA of 4,4-di-tert-butyl-3-nitromethyl-4H-[1,2]oxazete
Summary
Introduction because they pose useful inCyclic nitronates nitronates are are an animportant importantclass classofofcompounds compounds because they pose useful termediates ininthe intermediates thesynthesis synthesisofofcomplex complexnitrogen-containing nitrogen-containingscaffolds scaffolds due due to their high main methods of reactivity as 1,3-dipoles. Rizzardopresented presentedstudies studiesononthe the photochemistry α,β-unsaturated photochemistry of of α,β-unsaturated ninitro compounds [5]. They isolated thethe four-membered cyclic nitronates derivatives starting ing cis-α,4-dinitrostilbene, which breaks to benzaldehyde give benzaldehyde and pwithwith cis-α,4-dinitrostilbene, which breaks downdown to give and p-nitronitrobenzonitrile oxide The Authors do not present specific data data conconfirming structure of the obtained nitronate. Distributed under the terms and conLicensee MDPI, Basel, Switzerland.
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