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One-Pot Formation and Derivatization of Di- and Triynes Based on the Fritsch-Buttenberg-Wiechell Rearrangement

Thanh Luu, Yasuhiro Morisaki, Nina Cunningham and Rik R. Tykwinski*

*Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada, Email: rik.tykwinskiualberta.ca

T. Luu, Y. Morisaki, N. Cunningham, R. R. Tykwinski, J. Org. Chem., 2007, 72, 9622-9629.

DOI: 10.1021/jo701810g (free Supporting Information)


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Abstract

A carbenoid Fritsch-Buttenberg-Wiechell (FBW) rearrangement of a substituted dibromoolefinic precursor is used to generate a lithium acetylide, and subsequent trapping with carbon-based electrophiles provides a wide range of di- and triynes. The lithium acetylide formed from the FBW reaction can also undergo transmetalation to provide zinc, copper, tin, or platinum acetylides.

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Key Words

diynes, alkynes, propargyl alcohols, arenes, Fritsch-Buttenberg-Wiechell Rearrangement, Negishi Coupling, Hay Coupling


ID: J42-Y2007-4000