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- W2044693668 abstract "1,2-Dihydronaphthalin (1) wird von o- und p-Chinonen nach einem zweistufigen Mechanismus dehydriert. Die geschwindigkeitsbestimmende Abspaltung des Hydrid-Ions erfolgt bei o-Chlor-(4a) und o-Bromanil (4b) mit hoher Regioselektivität aus der 2-Stellung. Durch Fixierung der Ionen im engen Ionenpaar wird eine stereoselektive cis-Eliminierung des Protons bewirkt. Die Höhe der Stereoselektivität, der primären Isotopeneffekte und der Aktivierungsentropien sprechen für eine koplanare Anordnung der Moleküle im Übergangszustand sowie für einen deutlichen Tunnel-Anteil. p-Chinone zeigen eine andere Regioselektivität der Hydrid-Abstraktion. Die Dehydrierung des 9,10-Dihydrophenanthrens (3) läuft analog ab. Hydrogen Transfer Reactions, 6. Dehydrogenation of 1,2-Dihydroarenes by Quinones: Regio- and Stereoselectivity in the Two-Step Mechanism 1,2-Dihydronaphthalene (1) is dehydrogenated by o- and p-quinones in a two-step mechanism. In the rate determining step a hydride ion is abstracted from the 2-position by o-chloro- (4a) and o-bromoanil (4b) with high regioselectivity. Ion pairing leads to highly stereoselective cis-elimination of the proton. Stereoselectivity, primary isotope effects, and activation entropy are consistent with a coplanar coordination in the transition state and participation of tunneling. p-Quinones show different regioselectivity in the hydride abstraction step. The dehydrogenation of 9,10-dihydrophenanthrene (3) proceeds in a similar way." @default.
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- W2044693668 date "1985-07-01" @default.
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- W2044693668 title "Wasserstoffübertragungen, 6. Dehydrierungen von 1,2‐Dihydroarenen mit Chinonen: Regio‐ und Stereoselektivität der Teilschritte" @default.
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