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- W2001796111 abstract "Die Solvolyse von 2.6-Dimethyl-octanol-(5)-tosylat (6) und die Desaminierung von 5-Amino-2.6-dimethyl-octan (7) — beide mit S-Konfiguration an C-6 — lieferte neben anderen Produkten (R)-2.6-Dimethyl-octanol-(6) (8) (Tetrahydrolinalool). Die Konfigurations-erhaltung am Ausgangspunkt der 1,2-Wasserstoff-Verschiebung betrug in beiden Reaktionen ca. 60%. Ebenso führte die Desaminierung von (S)-2-Methyl-6-aminomethyl-octan (14) zu (R)-8 (41% Konfigurationserhaltung). Mögliche Ursachen für das chirale Verhalten des umgelagerten Carbonium-Ions werden diskutiert. Stereochemistry of Aliphatic Carbonium Ions, 4. Hydride Shifts in the 2.6-Dimethyloctyl System The solvolysis of 2,6-dimethylocatan-5-ol tosylate (6) and the deamination of 5-amino-2,6-dimethyloctane (7) — both of S-configuration at C-6 — afforded among other products (R)-2,6-dimethyloctan-6-ol (8) (tetrahydrolinalool). Both reactions proceeded with ca. 60% retention (40% racemization) at the migration origin of the 1,2 hydride shift. The deamination of (S)-6-(aminomethyl)-2-methyloctane (14) also produced (R)-8 (41% retention). Various explanations of the chiral properties of the rearranged carbonium ion are discussed." @default.
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- W2001796111 date "1971-06-01" @default.
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- W2001796111 title "Stereochemie aliphatischer Carbonium-Ionen, 4. Wasserstoff-Verschiebung im 2.6-Dimethyl-octyl-System" @default.
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- W2001796111 doi "https://doi.org/10.1002/cber.19711040614" @default.
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