A Novel Method of CC-Bond Formation: Thermolytic Elimination of Sulfur and Hydrogen Halides from α-Halosulfides

A three‐step synthesis of the acrylic acid or acrylonitrile derivatives (2) uses thiols and α‐halocarboxylic acids or ‐nitrites as starting materials. The central intermediates are the α‐halosulfides (1), which give (2) on gas‐phase pyrolysis: the mechanism of this rearrangement resembles that of th...

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Veröffentlicht in:Angewandte Chemie International Edition 1981-06, Vol.20 (6-7), p.585-586
Hauptverfasser: Pommelet, Jean-Claude, Nyns, Claire, Lahousse, Francis, Merényi, Robert, Viehe, Heinz G.
Format: Artikel
Sprache:eng
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Zusammenfassung:A three‐step synthesis of the acrylic acid or acrylonitrile derivatives (2) uses thiols and α‐halocarboxylic acids or ‐nitrites as starting materials. The central intermediates are the α‐halosulfides (1), which give (2) on gas‐phase pyrolysis: the mechanism of this rearrangement resembles that of the Ramberg‐Bäcklund reaction.
ISSN:0570-0833
1521-3773
DOI:10.1002/anie.198105851