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• W2163399182 abstract "Quadricyclan (1a) wird mit dem Komplex aus Butyllithium und Tetramethylethylendiamin oder mit einer Mischung aus Butyllithium und Kalium-tert-butylat in hoher Ausbeute an der 1-Position zu 1b metalliert, über das zahlreiche 1-substituierte Quadricyclane zugänglich werden. 1-Chlorquadricyclan (11) liefert mit Organolithiumbasen, Lithiumamiden und mit Lithium-ethylthiolat (mit diesem aber nur in Gegenwart einer sperrigen Hilfsbase) nucleophile Substitutionsprodukte, die zu den entsprechenden Norbornadienen isomerisiert werden können. Mechanistische Untersuchungen zeigen, daß 1,7- und auch 1,5-Dehydroquadricyclan (4 und 5) als reaktive Zwischenstufen auftreten. Die mit 96% Racemisierung ablaufende nucleophile Substitution von optisch aktivem 1-Chlorquadricyclan mit Lithiumdimethylamid ist mit dem Eliminierungs-Additions-Mechanismus über 4 und 5 voll im Einklang. Nuclephilic Exchange Reactions at 1-Chloroquadricyclane: 1,5- and 1,7-Dehydroquadricyclane as Reactive Intermediates Quadricyclane was metalated at position 1 to 1b in high yield by the complex of butyllithium and tetramethylethylenediamine or by a mixture of butyllithium and potassium tert-butoxide. Numerous 1-substituted quadricyclanes were accessible via 1b. Nucleophilic substitution products were obtained by the reaction of 1-chloroquadricyclane with organolithium compounds, lithium amides, and with lithium ethylthiolate (in the presence of a bulky strong base), which could be isomerized to the corresponding norbornadienes. Mechanistic investigations have shown that 1,7-and 1,5-dehydroquadricyclane (4 and 5) were involved as reactive intermediates. The nucleophilic substitution of optical active 1-chloroquadricyclane with lithium dimethylamide proceeded with 96% racemization. This result is in accord with an elimination-addition mechanism passing over 4 and 5." @default.
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• W2163399182 date "1983-06-01" @default.
• W2163399182 modified "2023-10-12" @default.
• W2163399182 title "Nucleophile Austauschreaktionen am 1‐Chlorquadricyclan: 1,5‐ und 1,7‐Dehydroquadricyclan als reaktive Zwischenstufen" @default.
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• W2163399182 doi "https://doi.org/10.1002/cber.19831160612" @default.
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