405064-62-2Relevant academic research and scientific papers
Modification of the Fritsch-Buttenberg-Wiechell rearrangement: A facile route to unsymmetrical butadiynes
Chernick, Erin T,Eisler, Sara,Tykwinski, Rik R
, p. 8575 - 8578 (2001)
A modification of the Fritsch-Buttenberg-Wiechell rearrangement has been used to form unsymmetrically substituted 1,3-butadiynes from 1,1-dibromo-olefin precursors. The reaction proceeds via lithium-halogen exchange, followed by migration of the aryl or alkynyl moiety to provide the butadiyne framework. The facile formation of the dibromo-olefins in three steps from commercially available aryl aldehydes or carboxylic acid chlorides makes this procedure an attractive alternative to traditional methods for butadiyne synthesis.
Synthesis of unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes via alkylidene carbenoid rearrangements
Shi Shun, Annabelle L. K.,Chernick, Erin T.,Eisler, Sara,Tykwinski, Rik R.
, p. 1339 - 1347 (2007/10/03)
Unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes are synthesized in four steps from commercially available aldehydes or carboxylic acids. The key step in this process involves a Fritsch-Buttenberg-Wiechell rearrangement, in which an alkylidene carbenoid intermediate subsequently rearranges to the desired polyyne. This rearrangement proceeds under mild conditions, and it is tolerant of a range of functionalities. In general, the procedurally facile formation of the dibromoolefinic precursors, in combination with the effectiveness of the rearrangement step, makes this procedure an attractive alternative to traditional methods for di- and triyne synthesis that utilize palladium or copper catalysis.
