Journal
CHEMICAL COMMUNICATIONS
Volume 46, Issue 19, Pages 3235-3249Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c003170d
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Funding
- University of Alberta
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- German Academic Exchange Service
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The Fritsch-Buttenberg-Wiechell rearrangement of carbene/carbenoid intermediates has evolved into a valuable synthetic methodology for the preparation of polyyne structures. Various synthetic routes toward the formation of the corresponding precursors, alkynyl-substituted dibromoolefins, have been developed. Additionally, the scope of this methodology is expanded significantly by the development of functional group-tolerant one-pot procedures. The preparation of various polyynes up to the octa- and decaynes is, thus, possible on a scale that enables thorough physico-chemical characterization. Hence, series of polyynes have been investigated by, e. g., UV-vis, IR- and Raman spectroscopy, as well as X-ray crystallography. These investigations give unique insight into the structural characteristics of longer polyynes and hint to the structure of carbyne.
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