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- W2149041724 abstract "Trimethylgermyl-, Trimethylstannyl- und Trimethylplumbyl-diazoessigsäureäthylester (3 bzw. 4 bzw. 5) wurden synthetisiert und photochemisch zu [Trimethylgermyl]-, [Trimethylstannyl]-und [Trimethylplumbyl]-[äthoxycarbonyl]-carben (8 bzw. 9 bzw. 10) zersetzt. Die Carbene sind zur C–H-Einschiebung und zur Addition an die olefinische Doppelbindung befähigt. Die Cycloaddition vollzieht sich bei 9 völlig, bei 8 und 10 nahezu ganz cis-stereospezifisch. Im Augenblick der Reaktion besitzen die Carbene also einen Singulett-Zustand, der wegen des „Schweratomeffektes'' der Metallatome der Grundzustand sein sollte. Aus den Resultaten ist zu schließen, daß eine Äthoxycarbonylgruppe die Entartung der beiden Carben-p-Orbitale aufhebt. – Mit cis-2-Buten entstehen die diastereomeren Addukte 16c–18c und 16d–18d jeweils in fast gleichen Mengen. Metal-substituted Carbenes and C-metalated Diazoalkanes, V1). – Trimethylgermyl-, Trimethylstannyl-, and Trimethylplumbyl-ethoxycarbonyl Carbenes from Ethyl Trimethylmetallyl Diazoacetates Ethyl-trimethylgermyl-, -trimethylstannyl-, and -trimethylplumbyl-diazoacetate (3, 4, and 5, respectively) were synthesized and photolytically cleaved to [trimethylgermyl]-, [trimethylstannyl]-and [trimethylplumbyl]-[ethoxycarbonyl]-carbenes (8, 9, and 10, respectively). The carbenes insert into the C – H-bond and add to olefinic double bonds. The addition occurs completely (9) or almost completely (8, 10) cis-stereospecifically. The carbenes react in their singlet state, which, because of the heavy atom effect, ought to be the ground state. The results suggest a singlet ground state also for ethoxycarbonyl-carbene. – With cis-2-butene the diastereomers 16c–18c and 16d–18d are formed in nearly equal amounts." @default.
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- W2149041724 date "1972-09-29" @default.
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- W2149041724 title "Metallsubstituierte Carbene undC-metallierte Diazoalkane, V. Trimethylgermyl-, Trimethylstannyl- und Trimethylplumbyl-äthoxycarbonylcarben aus Trimethylmetallyl-diazoessigsäureäthylestern" @default.
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- W2149041724 doi "https://doi.org/10.1002/jlac.19727610117" @default.
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