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- W1966851813 abstract "Eine Reihe von Natriumsalzen CH-acider Carbonyl- und Nitroverbindungen ergeben mit 7-Oxo-7H-benzocyclohepten-6,8-dicarbonsaure-dimethylester (1) Michael-Addukte. Bei Temperaturen um 0°C entstehen unter Addition an nur eine Doppelbindung von 1 die Natriumenolate 2, welche sich zu den C-5-substituierten 7-Hydroxy-5H-benzocyclohepten-6,8-dicarbonsaureestern 3 protonieren lassen. Die 5H-Benzocycloheptene 3, und zwar als Anionen 2, lassen sich in siedendem Methanol in einer intramolekularen Michael-Addition zu den C-10-substituierten 7-Hydroxy-8,9-dihydro-5,9-methano-5H-benzocyclohepten-6,8-dicarbonsaureestern 4 cyclisieren. Die Stereochemie der Michael-Addukte 4 wird NMR-spektroskopisch und durch Abbau zu den 6,7,8,9-Tetrahydro-5,9-methano-5H-benzocyclohepten-7-onen 5 aufgeklart.Michael Addition of CH-Acidic Carbonyl and Nitro Compounds to 7-Oxo-7H-benzocycloheptene-6,8-dicarboxylic Ester.Some sodium salts of CH-acidic carbonyl and nitro compounds react with dimethyl 7-oxo-7H-benzocycloheptene-6,8-dicarboxylate (1) to give Michael adducts. At temperatures of about 0°C addition occurs at only one double bond of 1 to yield the sodium enolates 2 which give the C-5-substituted dimethyl 7-hydroxy-5H-benzocycloheptene-6,8-dicarboxylates 3 on protonation. The 5H-benzocycloheptenes 3, or more precisely their anions 2, are cyclized in boiling methanol in an intramolecular Michael addition to yield the C-10-substituted dimethyl 7-hydroxy-8,9-dihydro-5,9-methano-5H-benzocycloheptene-6,8-dicarboxylates 4. The stereochemistry of the Michael adducts 4 is elucidated by their NMR spectra and by degradation to the 6,7,8,9-tetrahydro-5,9-methano-5H-benzocyclohepten-7-ones 5." @default.
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- W1966851813 date "1973-12-13" @default.
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- W1966851813 title "Michael-Addition CH-acider Carbonyl- und Nitroverbindungen an 7-Oxo-7H-benzocyclohepten-6,8-dicarbonsäureester" @default.
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- W1966851813 doi "https://doi.org/10.1002/jlac.197319731109" @default.
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