41144-60-9Relevant academic research and scientific papers
One-pot synthesis and functionalization of polyynes via alkylidene carbenoids
Luu, Thanh,Morisaki, Yasuhiro,Tykwinski, Rik R.
, p. 1158 - 1162 (2008/12/22)
A one-pot, two-step method for the synthesis of diynes and triynes is reported. The reaction of a dibromoolefinic precursor with BuLi effects a Fritsch-Buttenberg-Wiechell rearrangement and generates a lithium acetylide intermediate, which is then trapped
One-pot formation and derivatization of di- and triynes based on the Fritsch-Buttenberg-Wiechell rearrangement
Luu, Thanh,Morisaki, Yasuhiro,Cunningham, Nina,Tykwinski, Rik R.
, p. 9622 - 9629 (2008/03/15)
(Chemical Equation Presented) 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 gene
Decarboxylative elimination of enol triflates as a general synthesis of acetylenes.
Fleming, Ian,Ramarao, Chandrashekar
, p. 1504 - 1510 (2007/10/03)
The enol trifluoromethanesulfonates 4, 8, 12, 17 and 20 of tert-butyl beta-ketodiesters and beta-ketoesters can be hydrolysed to the corresponding carboxylic acids by dissolution in trifluoroacetic acid. The dicarboxylic acids undergo mild decarboxylative elimination to give the acetylenic acids 4 and 9 in aqueous sodium bicarbonate solution at room temperature. Similarly, the monocarboxylic acids give the terminal and mid-chain acetylenes 13, 18, 21, and 24 by refluxing in acetone with potassium carbonate. One of the substituents on the acetylenes can be methyl, primary alkyl, secondary alkyl or ethynyl, and the other can be a carboxylic acid, hydrogen or primary alkyl, but the enol trifluoromethanesulfonates could not be prepared when one of the substituents was tert-butyl, nor when both substituents on the precursor to the acetylene were secondary alkyl.
