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• W2012255189 endingPage "7164" @default.
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• W2012255189 abstract "The heavier group 13 element alkene analogue, digallene AriPr4GaGaAriPr4 (1) [AriPr4 = C6H3-2,6-(C6H3-2,6-iPr2)2], has been shown to react readily in [n + 2] (n = 6, 4, 2 + 2) cycloaddition reactions with norbornadiene and quadricyclane, 1,3,5,7-cyclooctatetraene, 1,3-cyclopentadiene, and 1,3,5-cycloheptatriene to afford the heavier element deltacyclane species AriPr4Ga(C7H8)GaAriPr4 (2), pseudoinverse sandwiches AriPr4Ga(C8H8)GaAriPr4 (3, 3iso), and polycyclic compounds AriPr4Ga(C5H6)GaAriPr4 (4) and AriPr4Ga(C7H8)GaAriPr4 (5, 5iso), respectively, under ambient conditions. These reactions are facile and may be contrasted with other all-carbon versions, which require transition-metal catalysis or forcing conditions (temperature, pressure), or with the reactions of the corresponding heavier group 14 species AriPr4EEAriPr4 (E = Ge, Sn), which give very different product structures. We discuss several mechanistic possibilities, including radical- and non-radical-mediated cyclization pathways. These mechanisms are consistent with the improved energetic accessibility of the LUMO of the heavier group 13 element multiple bond in comparison with that of a simple alkene or alkyne. We show that the calculated frontier molecular orbitals (FMOs) of AriPr4GaGaAriPr4 are of π–π symmetry, allowing this molecule to engage in a wider range of reactions than permitted by the usual π–π* FMOs of C–C π bonds or the π–n+ FMOs of heavier group 14 alkyne analogues." @default.
• W2012255189 created "2016-06-24" @default.
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• W2012255189 date "2012-04-11" @default.
• W2012255189 modified "2023-10-16" @default.
• W2012255189 title "Reversible and Irreversible Higher-Order Cycloaddition Reactions of Polyolefins with a Multiple-Bonded Heavier Group 13 Alkene Analogue: Contrasting the Behavior of Systems with π–π, π–π*, and π–n₊ Frontier Molecular Orbital Symmetry" @default.
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• W2012255189 doi "https://doi.org/10.1021/ja301247h" @default.
• W2012255189 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/22420622" @default.
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