Dienophilic reactivity of 2-phosphaindolizines: a conceptual DFT investigation

• Nosheen Beig,
• Aarti Peswani and
• Raj Kumar Bansal

Beilstein J. Org. Chem. 2022, 18, 1217–1224, doi:10.3762/bjoc.18.127

• ) calculations have been used in recent years to predict the reactivity of organic molecules in reactions. We calculated global hardness (η), global softness (S), electronic chemical potential (μ), electrophilicity (ω), and nucleophilicity (N) indices of four classes of 2-phosphaindolizines, on the basis of

• reactivities observed experimentally. Furthermore, energies and symmetries of the lowest unoccupied molecular orbitals (LUMO) of 2-phosphaindolizines were found to be in conformity with their dienophilic reactivities. Keywords: dienophilic reactivity; electronic chemical potential; electrophilicity index

• ), global softness (S), electronic chemical potential (µ), electrophilicity (ω) and nucleophilicity (N) indices of 2-phosphaindolizines 6 and 1,3-butadiene (7) are given in Table 2. 2-Phosphaindolizines and 1,3-butadiene are soft electrophiles and nucleophile, respectively, and in accordance with the HSAB

Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple

• Alexander S. Filatov,
• Olesya V. Khoroshilova,
• Anna G. Larina,
• Vitali M. Boitsov and
• Alexander V. Stepakov

Beilstein J. Org. Chem. 2022, 18, 769–780, doi:10.3762/bjoc.18.77

• (2m) and corresponding DFT calculations (relative Gibbs free energy change between reagents, transition states and possible invertomers are given in kcal/mol). Optimization of the reaction conditionsa,b. FMO energies (a.u.), electronic chemical potential (μ, eV), chemical hardness (η, eV), and global