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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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1865-7117
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Volume 73, Issue 7

Issues

Orthoamide und Iminiumsalze, XCIII. Darstellung und Umsetzungen eines vinylogen Orthoamid-Derivats der Kohlensäure mit CH2-aciden Verbindungena

Orthoamides and Iminium Salts XCIII. Preparation and reactions of a vinylogue orthocarbonic acid amide derivative with CH2-acidic compoundsa

Markus Vettel
  • Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany
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/ Hans-Jürgen Bräuner
  • Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany
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/ Willi Kantlehner
  • Corresponding author
  • Institut für Angewandte Forschung, Abteilung Technische Organische Synthesechemie und Katalyseforschung (TOSKA), Hochschule Aalen, Beethovenstr. 1, D-73430 Aalen, Germany; and Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany, Fax: +49-7361-5762250
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Published Online: 2018-06-30 | DOI: https://doi.org/10.1515/znb-2018-0022

Abstract

The preparation of the vinylogue guanidinium salt 10c is described. The reaction of the vinylogue orthocarbonic acid amide derivative 12 with CH2-acidic compounds 14a–s affords the ketene aminals 15a–s. At room temperature the succinimide 19a is deprotonated by 12 to give the vinylogue salt 10e. The bis-ketene aminal 20 is formed in the reaction of 19a with 12 at elevated temperatures. Succinic acid esters 21 do not react cleanly with the orthoamide 12, but mixtures of ketene aminals 23 and bis-ketene aminals 22 are formed. From succinodinitrile (24) and 12 the bis-ketene aminal 25 could be obtained, which is also accessible by the action of the salt 10c with 24 in the presence of sodium hydride.

Keywords: CH2-acidic compounds; condensation reactions; ketene aminals; orthocarbonic acid amide; vinylogue guanidinium salt

Dedicated to:

Professor Branko Stanovnik on the occasion of his 80th birthday.

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About the article

aOrthoamide und Iminiumsalze XCII: siehe Lit. [1]


Received: 2018-02-03

Accepted: 2018-02-19

Published Online: 2018-06-30

Published in Print: 2018-07-26


Citation Information: Zeitschrift für Naturforschung B, Volume 73, Issue 7, Pages 457–466, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2018-0022.

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