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

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
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Publikationsverlauf

Received: 16. Februar 2012

Accepted after revision: 10. Juli 2012

Publikationsdatum:
09. August 2012 (online)


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.

 
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