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Synfacts 2010(12): 1368-1368  
DOI: 10.1055/s-0030-1258941
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

A New Route to Diaminoacetylenes

Contributor(s): Timothy M. Swager, Shuang Liu
A. R. Petrov, C. G. Daniliuc, P. G. Jones, M. Tamm*
Technische Universität Braunschweig, Germany
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Publikationsdatum:
22. November 2010 (online)

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Significance

Inspired by the preparation of diaryl-acetylenes, a general synthetic approach to diaminoacetylenes (ynediamines) has been developed based on the Fritsch-Buttenberg-Wiechell rearrangement. Both aromatic and aliphatic diaminoacetylenes 5 can be synthesized conveniently in moderate to high yields. X-ray crystal structures of the diaminoacetylenes (5a and 5b) have been determined for the first time, confirming the theoretical prediction that the two NC3 planes are almost perpendicular.