Issue 19, 2010

The Fritsch–Buttenberg–Wiechell rearrangement: modern applications for an old reaction

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.

Graphical abstract: The Fritsch–Buttenberg–Wiechell rearrangement: modern applications for an old reaction

Article information

Article type
Feature Article
Submitted
15 Feb 2010
Accepted
04 Mar 2010
First published
14 Apr 2010

Chem. Commun., 2010,46, 3235-3249

The Fritsch–Buttenberg–Wiechell rearrangement: modern applications for an old reaction

E. Jahnke and R. R. Tykwinski, Chem. Commun., 2010, 46, 3235 DOI: 10.1039/C003170D

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