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• W1990709255 abstract "Die symmetrisch substituierten tertiären Phosphanoxide 5 wurden aus den Phosphorhalogeniden 4 sowie 6 und metallorganischen Reagenzien erhalten. Dibenzylphenylphosphanoxid (5c) reagierte mit Brom bei 150°C zu den drei möglichen diastereomeren α,α′-Dibromphosphanoxiden (R,R/S,S)-2c, (r)-2c und (s)-2c und einem α-Bromphosphanoxid 8. Die Phosphanoxide 5a,b,d ließen sich durch Butyllithium in den α-Stellungen einfach oder doppelt lithiieren. Die α,α′-dilithiierten Phosphanoxide [Li2]-5 reagierten mit Tetrachlormethan unterhalb −80°C zu den α-Chlorphosphanoxiden 1c–e, deren Diastereomerenverhältnis kinetisch kontrolliert war. Mit Basen wurde das thermodynamische Diastereomerenverhältnis eingestellt. Während die α-lithiierten Dineopentylphosphanoxide [Li]-5a und [Li]-5d mit überschüssigem Tetrachlormethan ebenfalls 1c bzw. 1d bildeten, entstand aus dem α-Lithiodibenzylphosphanoxid [Li]-5b das α,α-Dichlorphosphanoxid 9. Dieser Unterschied wird auf die Acidität der α-Protonen und auf sterische Faktoren zurückgeführt. Die Konfiguration und Vorzugskonformation der α,α′-Dibromphosphanoxide 2c und der α-Chlorphosphanoxide 1c–e wurde anhand der 1H-31P-Kopplung der Methinprotonen bestimmt. Three-membered Ring Heterocycles, 14. α-Halogenation of Tertiary Phosphane Oxides The symmetrically substituted tertiary phosphane oxides 5 were obtained from the phosphorus halides 4 and 6 using organometallic reagents. Dibenzylphenylphosphane oxide (5c) reacted with bromine at 150°C to give all three possible diastereomeric α,α′-dibromophosphane oxides, e.g. (R,R/S,S)-2c, (r)-2c, and (s)-2c, and one α-bromophosphane oxide 8. The phosphane oxides 5a,b,d were lithiated once or twice in the α-positions by means of butyllithium. The α,α′-dilithiophosphane oxides [Li2]-5 reacted with tetrachloromethane below −80°C to yield the α-chlorophosphane oxides 1c–e whose diastereomeric ratios were controlled kinetically. The thermodynamically controlled ratios were adjusted with bases. While the α-lithiated dineopentylphosphane oxides [Li]-5a and [Li]-5d also afforded the α-chlorophosphane oxides 1c and 1d, respectively, with an excess of tetrachloromethane, the α,α-dichlorophosphane oxide 9 was formed from the α-lithiodibenzylphosphane oxide [Li]-5b. This difference is attributed to the acidity of the α-protons and steric factors. The configurations and preferred conformations of the α,α′-dibromophosphane oxides 2c and the α-chlorophosphane oxides 1c–e were determined on the basis of the 1H-31P coupling of the methine protons." @default.
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• W1990709255 date "1982-10-01" @default.
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• W1990709255 title "Dreigliedrige Heterocyclen, 14. α‐Halogenierung von tertiären Phosphanoxiden" @default.
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• W1990709255 doi "https://doi.org/10.1002/cber.19821151015" @default.
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