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Photolyse von aliphatischen Säurechloriden in Diäthyläther

Photoreactions of carboxylic acid derivatives, VIII.: Photolysis of aliphatic acyl chlorides in ethereal solutions

Lichtreaktionen mit Carbonsäurederivaten, 8. Mitt.

  • Organische Chemie und Biochemie
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Abstract

On photolysis of acetyl chloride (wave length 254 nm) in ethereal solution the main product is 3-ethoxy-2-butanone (1). The by-products are 2.3-diethoxy-butane (3), butane-2.3-dione, ethyl acetate and 3-acetoxy-2-butanone.1 is formed by the substitution of ether by the radical pair (CH3CO·· Cl) within the solvent cage. Diffusion of the radical pair from the cage causes H-abstraction from the ether forming the α-ether radical2. The letter combines to3. The ratio of1 to3 depends on temperature.

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Literatur

  1. U. Schmidt undH. Egger, Radiation and Photochemistry of Carbonyl Halides, in:S. Patai (Hrsg.), The Chemistry of Carbonyl Halides. London-New York-Sydney-Toronto: Interscience. 1971.

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  2. U. Schmidt, Angew. Chem.77, 196 (1965).

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  3. U. Schmidt, Angew. Chem.77, 216 (1965).

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Authors and Affiliations

  1. Institut für Organische Chemie der Universität Wien, Währinger Straße 38, A-1090, Wien, Österreich

    A. Nikiforov & U. Schmidt

Authors
  1. A. Nikiforov
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  2. U. Schmidt
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Herrn Prof. Dr.O. Hoffmann-Ostenhof mit freundlichen Grüßen gewidmet.

Mit 1 Abbildung

7. Mitt.:W. Silhan undU. Schmidt, Mh. Chem.102, 1481 (1971).

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Nikiforov, A., Schmidt, U. Photolyse von aliphatischen Säurechloriden in Diäthyläther. Monatshefte für Chemie 105, 1044–1049 (1974). https://doi.org/10.1007/BF00910271

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  • DOI: https://doi.org/10.1007/BF00910271

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