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Synthesis 2011(4): 642-652  
DOI: 10.1055/s-0030-1258399
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

On the Synthesis of Arylpropiolic Acids and Investigations towards the Formation of Vinyl Chlorides by HCl Addition During Esterification Reactions

Marko Hapke*, Karolin Kral, Anke Spannenberg
Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Fax: +49(831)128151213; e-Mail: marko.hapke@catalysis.de;
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Publication History

Received 16 November 2010
Publication Date:
10 January 2011 (online)

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Abstract

The synthesis protocol for the preparation of different arylpropiolic acids using the Negishi reaction and the addition of HCl to the alkyne moiety of these acids in subsequent esterification reactions using SOCl2 was examined.

Key words

alkynes - esterification - addition reactions - vinyl chlorides - Negishi reaction

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7

The crystallographic data for compound 6 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 797405. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk].