One-pot formation and derivatization of di-and triynes based on the Fritsch-Buttenberg-Wiechell rearrangement

T Luu, Y Morisaki, N Cunningham…

Index: Luu, Thanh; Morisaki, Yasuhiro; Cunningham, Nina; Tykwinski, Rik R. Journal of Organic Chemistry, 2007 , vol. 72, # 25 p. 9622 - 9629

Full Text: HTML

Citation Number: 49

Abstract

A divergent, one-pot synthesis of functionalized polyynes has been developed. Beginning with the appropriately substituted dibromoolefinic precursor, a carbenoid Fritsch-Buttenberg- Wiechell (FBW) rearrangement is used to generate the lithium acetylide of a conjugated polyyne framework, and subsequent trapping with carbon-based electrophiles provides for in situ formation of a wide range of di-and triynes. The lithium acetylide formed from the ...

Related Articles:

Contingency and serendipity in the reactions of Fischer carbene complexes with conjugated triynes

[Jiang, May Xiao-Wu; Rawat, Manish; Wulff, William D. Journal of the American Chemical Society, 2004 , vol. 126, # 19 p. 5970 - 5971]

Solution-spray flash vacuum pyrolysis: a new method for the synthesis of linear poliynes with odd numbers of C. tplbond. C bonds from substituted 3, 4-dialkynyl-3- …

[Rubin, Yves; Lin, Sophia S.; Knobler, Carolyn B.; Anthony, John; Boldi, Armen M.; Diederich, Francois Journal of the American Chemical Society, 1991 , vol. 113, # 18 p. 6943 - 6949]

Investigation of an Efficient Palladium-Catalyzed C (sp)− C (sp) Cross-Coupling Reaction Using Phosphine− Olefin Ligand: Application and Mechanistic Aspects

[Shi, Wei; Luo, Yingdong; Luo, Xiancai; Chao, Lei; Zhang, Heng; Wang, Jian; Lei, Aiwen Journal of the American Chemical Society, 2008 , vol. 130, # 44 p. 14713 - 14720]

Contingency and serendipity in the reactions of Fischer carbene complexes with conjugated triynes

[Jiang, May Xiao-Wu; Rawat, Manish; Wulff, William D. Journal of the American Chemical Society, 2004 , vol. 126, # 19 p. 5970 - 5971]

Contingency and serendipity in the reactions of Fischer carbene complexes with conjugated triynes

[Jiang, May Xiao-Wu; Rawat, Manish; Wulff, William D. Journal of the American Chemical Society, 2004 , vol. 126, # 19 p. 5970 - 5971]

More Articles...