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Synthesis 1997; 1997(5): 573-588
DOI: 10.1055/s-1997-1221
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3,3-Dichloroprop-2-ene Iminium Salts (Vinylogous Viehe Salts): A Study of Their Reactivity Towards Nucleophiles

Ullrich Jahn, Jens Andersch, Werner Schroth*
  • *Institut für Organische Chemie der Martin-Luther-Universität Halle-Wittenberg, Kurt-Mothes-Straße 2, D-06099 Halle (Saale), Germany, Fax +49(345)5527030
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Publication Date:
31 December 2000 (online)

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The title compounds 3 react regioselectively at either the 1- or 3-position depending on the reaction partner. Chloro substitution affording new propene iminium salts is preferred e.g. in the reaction with mercaptans (to 10, 11), amines (to 7, 14, 15), and some activated arenes and hetarenes (to 26, 27). Nucleophilic attack at the 1-position providing an allyl or allylidene structure is observed e.g. in the reaction with water (to 4), alcohol (to 6), trialkyl phosphite (to 21, 22), trimethylsilyl cyanide (to 30), Grignard reagents (to 31), and acceptor activated methylene compounds (to 33-44). Reaction at both positions with heterocyclization to 13 occurs with thioamide functions. The regiochemistry depends on a complex interplay of several factors in contrast to the FMO predicted orientation. The utility of 3 and some consecutive products as versatile C3-building blocks for further syntheses is foreseeable.

iminium salts - ambident reactivity - regioselectivity - nucleophilic addition/substitution - C3-building blocks