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• W2152842567 abstract "Alkylation versus electron transfer: Polyaromatic hydrocarbon dianions (PAHs−2) react with fluoroalkanes in a nucleophilic fashion in spite of being generally regarded as powerful electron-transfer reagents (see graphic). The regiochemistry of the reductive alkylations can be easily predicted by simple MO calculations. Some of the most highly reduced organic species in solution, such as the dianions of PAHs (polycyclic aromatic hydrocarbons) display unexpected reactivity patterns when they react with an appropriate counterpart. As seen before in their reaction with propene and other alkenes, PAHs−2 apparently react with fluoroalkanes in a nucleophilic fashion in spite of being generally regarded as powerful electron-transfer reagents in their reactions with haloalkanes. This methodology complements the current methodologies on reductive alkylation of polycyclic arenes by allowing access to a new set of regioisomers, the regiochemistry of which can be easily predicted by simple MO calculations. Algunas de las especies orgánicas más reducidas en disolución, como los dianiones de HAP (hidrocarburo aromático policíclico), muestran patrones de reactividad imprevistos cuando reaccionan con el sustrato apropiado. Tal y como se vio anteriormente frente a propeno y otros alquenos, los HAP−2 reaccionan aparentemente como nucleófilos con fluoruros de alquilo, a pesar de ser considerados generalmente como poderosos agentes de transferencia electrónica frente a halogenuros de alquilo. Esta metodología complementa las actuales metodologías de alquilación reductora de arenos policíclicos, permitiendo el acceso a un nuevo grupo de regioisómeros, cuya regioquímica puede ser fácilmente predicha por medio de simples cálculos de orbitales moleculares. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2111/2007/f700187_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article." @default.
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• W2152842567 date "2007-12-17" @default.
• W2152842567 modified "2023-10-18" @default.
• W2152842567 title "New Modes of Reactivity in the Threshold of the Reduction Potential in Solution. Alkylation of Lithium PAH (Polycyclic Aromatic Hydrocarbon) Dianions by Primary Fluoroalkanes: A Reaction Pathway Complementing the Classical Birch Reductive Alkylation" @default.
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• W2152842567 doi "https://doi.org/10.1002/chem.200700187" @default.
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