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- W2022367461 abstract "Die Carbonyl-C-Atome von Ketonen (Aceton, Cyclohexanon) und Aldehyden (Propanal, 2,2-Dimethylpropanal, Acrolein, Benzaldehyd und p-Methoxybenzaldehyd) wurden über ein – von Tetrabrommethan stammendes – Kohlenstoffatom zu trisubstituierten Allenen verknüpft (9 und 10, siehe Schema 1). Die Reaktionssequenz besteht dabei aus vier Schritten: a) Olefinierung des Ketons zu einem 1,1-Dibromalken (1, 2); b) Br/Li-Austausch bei – 105 °C und Addition des entstehenden Brom-lithium-carbenoids (3, 4) an einen Aldehyd zum allylischen Bromhydrin (5, 6); c) O-Silylierung zum Silylether (7, 8); d) Eliminierung mit tert-Butyllithium zum Allen (9, 10). Preparation of Allenes from Geminal Dibromo Olefins and Aldehydes The carbonyl carbons of ketones (acetone, cyclohexanone) and aldehydes (propanal, 2,2-dimethylpropanal, acrolein, benzaldehyde, p-methoxybenzaldehyde) are joined through a single carbon atom (originating from carbon tetrabromide) to give trisubstituted allenes (9 and 10, see Scheme 1). The sequence consists of four operational steps: (i) olefination of the ketone to a 1,1-dibromoalkene (1, 2); (ii) Br/Li-exchange at – 105°C and addition of the resulting bromolithio-carbenoid (3, 4) to the aldehyde to give an allylic bromohydrine (5, 6); (iii) silylation at oxygen (→ 7, 8) by treatment with chlorotrimethylsilane/hexamethyldisilazane/pyridine; (iv) elimination of the elements of BrOSiMe3 with tert-butylithium to produce the allenes (9, 10)." @default.
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- W2022367461 date "1984-05-01" @default.
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- W2022367461 title "Herstellung von Allenen aus geminalen Dibromolefinen und Aldehyden" @default.
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- W2022367461 doi "https://doi.org/10.1002/cber.19841170515" @default.
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