The Fritsch-Buttenberg-Wiechell rearrangement: Modern applications for an old reaction

Jahnke E, Tykwinski R (2010)


Publication Type: Journal article, Review article

Publication year: 2010

Journal

Original Authors: Jahnke E., Tykwinski R.R.

Publisher: Royal Society of Chemistry

Book Volume: 46

Pages Range: 3235-3249

Journal Issue: 19

DOI: 10.1039/c003170d

Abstract

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. © 2010 The Royal Society of Chemistry.

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How to cite

APA:

Jahnke, E., & Tykwinski, R. (2010). The Fritsch-Buttenberg-Wiechell rearrangement: Modern applications for an old reaction. Chemical Communications, 46(19), 3235-3249. https://doi.org/10.1039/c003170d

MLA:

Jahnke, Eike, and Rik Tykwinski. "The Fritsch-Buttenberg-Wiechell rearrangement: Modern applications for an old reaction." Chemical Communications 46.19 (2010): 3235-3249.

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