Synthesis 2012; 44(19): 3090-3094
DOI: 10.1055/s-0032-1316991
paper
© Georg Thieme Verlag Stuttgart · New York

Orthoamides and Iminium Salts LXXXII:[ 1 ] Cleavage of Orthoamides of Alkynecarboxylic Acids by Elemental Iodine – A New Method for the Preparation of Vinylogous Guanidinium Salts

Authors

  • Willi Kantlehner*

    a   Fakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstr. 1, 73430 Aalen, Germany, Fax: +49(7361)5762250   Email: willi.kantlehner@htw-aalen.de
    b   Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
  • Rüdiger Stieglitz

    b   Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
  • Ralf Kreß

    a   Fakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstr. 1, 73430 Aalen, Germany, Fax: +49(7361)5762250   Email: willi.kantlehner@htw-aalen.de
    b   Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
  • Wolfgang Frey

    b   Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
  • Ioannis Tiritiris

    a   Fakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstr. 1, 73430 Aalen, Germany, Fax: +49(7361)5762250   Email: willi.kantlehner@htw-aalen.de
    b   Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
Further Information

Publication History

Received: 16 February 2012

Accepted after revision: 10 July 2012

Publication Date:
09 August 2012 (online)


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Dedicated to Prof. Dr. Jean Sommer on the occasion of his 75th birthday

Abstract

Orthoamides of six alkynecarboxylic acids, possessing reactive substituents in 3-position, are transformed by elemental iodine to the corresponding vinylogous guanidinium iodides. The constitution of two of the iodides was established by crystal-structure­ analysis.