The Fritsch-Buttenberg-Wiechell rearrangement: modern applications for an old reaction.
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.
Jahnke
Eike
E
Institut für Organische Chemie, Friedrich-Alexander Universität Erlangen Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany.
Tykwinski
Rik R
RR
D008958:Models, Molecular; D015394:Molecular Structure; D053279:Polyynes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D053279:Polyynes