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- W2016334558 abstract "Elektrophile Diazoalkan-Substitution der (Diazomethyl)phosphoryl-Verbindungen 13a–d mit den 7-Alkoxybenzocycloheptenylium-perchloraten 8a–e liefert die 7-Alkoxy-5-(diazomethyl)-5H-benzocycloheptene 15a–l, die im allgemeinen schnell durch intramolekulare Cycloadditon zu den Tetracyclen 19a–l isomerisieren. Die beim primären Substitutionsprozeß ebenfalls gebildeten 7-Isomeren 14 lassen sich 1H-NMR-spektroskopisch nach-weisen. Durch thermische Stickstoff-Abspaltung werden 19a, b, e und h in die Tetracyclen 21a–d umgewandelt. Im Falle von 19i, k und l ist die Tetracyclen-Bildung noch von einer zusätzlichen hetero-Cope-Umlagerung begleitet (→22a–c). Die Umsetzung der lithiierten Diazomethyl-Verbindungen 24a und b mit 7-Morpholinobenzocycloheptenylium-perchlorat (23) führt nach chromatographischer Aufarbeitung zu den Ketonen 26a und b. Diazo Compounds, 701. – Intramolecular Cycloaddition of 5-(Diazomethyl)-5H-benzocycloheptenes – Partial Step of a New Benzosemibullvalene Synthesis Electrophilic diazoalkane substitution of the (diazomethyl)phosphoryl compounds 13a–d with the 7-alkoxybenzocycloheptenylium perchlorates 8a–e yields the 7-alkoxy-5-(diazomethyl)-5H-benzocycloheptenes 15a–l, which generally isomerize quickly by intramolecular cycloaddition to the tetracycles 19a–l. The 7-isomers 14, formed also in the primary substitution process, can be detected by 1H-NMR spectroscopy. By thermal nitrogen elimination, 19a, b, e, and h are transformed into the tetracycles 21a–d. In the case of 19i, k, and l the formation of the tricyclic compounds is accompanied by an additional hetero Cope rearrangement (→22a–c). The reaction of the lithiated diazomethyl compounds 24a and b with 7-morpholinobenzocycloheptenylium perchlorate (23) after chromatographic workup leads to the ketones 26a and b." @default.
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- W2016334558 title "Diazoverbindungen, 70. Intramolekulare Cycloaddition von 5-(Diazomethyl)-5H-benzocycloheptenen – Teilschritt einer neuen Benzosemibullvalen-Synthese" @default.
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- W2016334558 doi "https://doi.org/10.1002/cber.19891220327" @default.
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