Synthesis 2008(14): 2155-2157  
DOI: 10.1055/s-2008-1067141
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

[(3-Cyanopropyl)diisopropylsilyl]acetylene, a More Stable Analogue of [(3-Cyanopropyl)dimethylsilyl]acetylene

Gerald Gaefke, Sigurd Höger*
Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Fax: +49(228)735662; e-Mail: hoeger@uni-bonn.de;
Further Information

Publication History

Received 3 May 2008
Publication Date:
18 June 2008 (online)

Abstract

The preparation and application of a new alkyne protecting group is presented. The reactivity and stability of [(3-cyanopropyl)diisopropylsilyl]acetylene is similar to that of the well-known (triisopropylsilyl)acetylene. Its high polarity simplifies chromatographic separation after coupling to aromatics with more than one reactive site. Moreover, compounds with more than one [(3-cyanopropyl)diisopropylsilyl]acetylene group are easily purified after partial deprotection.