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Synfacts 2011(4): 0387-0387  
DOI: 10.1055/s-0030-1259635
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

[2,2]Paracyclophanes with New Bridges

Contributor(s): Timothy M. Swager, Olesya Haze
M. L. Birsa*, P. G. Jones, H. Hopf
Technische Universität Braunschweig, Germany and Alexandru Ioan Cuza University of Iasi, Romania
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Publication History

Publication Date:
18 March 2011 (online)

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Significance

The formal cyclotrimerization of pseudo-geminal bisacetylene 1 with a variety of acetylenes (2a-d) and nitriles 4a,b provides facile access to [2.2]paracyclophanes 3a-d and 5a,b with orthogonal π-bridges. Interestingly, the bridging does not drastically change the flattened boat conformation, but causes a nonparallel alignment of the paracyclophane rings according to an X-ray crystal structure analysis of 3a.