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- W2017881103 abstract "Die Alkylierung des Jodlactons 16 und des (Phenylthio)lactons 18 mit Triäthyloxonium-tetrafluoroborat unter Gleichgewichtsbedingungen sowie die intramolekulare Substitution des Dibromnorbornandiesters 14 in Gegenwart von Silber-tetrafluoroborat liefert Produktgemische, deren Verhältnisse von den in elektrophilen Additionen an 12 erhaltenen Isomerengemischen abweichen (s. Tab.). Das Bromlacton 20 und das Lacton 21 reagieren mit Triäthyloxonium-tetrafluoroborat unter diesen Bedingungen nicht. Dies läßt darauf schließen, daß für X = Br, J, H und C6H5S die Umlagerung 8 ⇌ 9 langsamer abläuft als die Bildung der Produkte 10 und 11. – Die Quecksilberacetat-Addition an den Diester 26 liefert ausschließlich die intermolekularen exo,cis-Abfangprodukte 27 und 28, während die Halbester 30 und 31 quantitativ zu den Lactonen 29 und 32 reagieren. Open and Bridged Intermediates, 5. The Mechanism of the Nucleophilic Competition Reaction in the System. Carboxylic Acid/Carboxylic Ester The alkylation of the iodolactone 16 and the (phenylthio)lactone 18 with triethyloxonium tetrafluoroborate under equilibrium conditions and the intramolecular substitution of the dibromonorbornanediester 14 in the presence of silver tetrafluoroborate yield mixtures of products whose ratios differ from those of isomers obtained in the electrophilic addition to 12 (table). The bromolactone 20 and the lactone 21 do not react with triethyloxonium tetrafluoroborate under these conditions. It is concluded that with X = Br, J, H, and C6H5S the rearrangement reaction 8 ⇌ 9 is slower than the formation of the products 10 and 11. – The mercuric acetate addition to the diester 26 yields the intermolecular trapping products 27 and 28 exclusively, whereas 30 and 31 react quantitatively to give the lactones 29 and 32." @default.
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- W2017881103 date "1975-09-01" @default.
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- W2017881103 title "Offene und verbrückte Zwischenstufen, 5. Zum Mechanismus der nucleophilen Konkurrenzreaktion im System Carbonsäure/Carbonester" @default.
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- W2017881103 doi "https://doi.org/10.1002/cber.19751080920" @default.
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