54811-48-2Relevant academic research and scientific papers
Unexpected reactivity of 3-(phenylethynyl)-1H-indenes towards nucleophiles: Noncatalytic addition to triple bond with or without double bond migration
Ivchenko,Nifant'ev,Luzikov,Mkoyan
, p. 1038 - 1046 (2007)
When studying the chemical properties of (3-phenylethynyl)-1H-indenes, a new reaction was discovered, namely, nucleophilic addition to conjugated enynes accompanied in some cases by migration. The reaction takes place under mild conditions and is not cata
Microwave-Assisted Organocatalyzed Rearrangement of Propargyl Vinyl Ethers to Salicylaldehyde Derivatives: An Experimental and Theoretical Study
Tejedor, David,Cotos, Leandro,Márquez-Arce, Daniel,Odriozola-Gimeno, Mikel,Torrent-Sucarrat, Miquel,Cossío, Fernando P.,García-Tellado, Fernando
supporting information, p. 18280 - 18289 (2015/12/24)
The microwave-assisted imidazole-catalyzed transformation of propargyl vinyl ethers (PVEs) into multisubstituted salicylaldehydes is described. The reaction is instrumentally simple, scalable, and tolerates a diverse degree of substitution at the propargylic position of the starting PVE. The generated salicylaldehyde motifs incorporate a broad range of topologies, spanning from simple aromatic monocycles to complex fused polycyclic systems. The reaction is highly regioselective and takes place under symmetry-breaking conditions. The preparative power of this reaction was demonstrated in the first total synthesis of morintrifolin B, a benzophenone metabolite isolated from the small tree Morinda citrifolia L. A DFT study of the reaction was performed with full agreement between calculated values and experimental results. The theoretically calculated values support a domino mechanism comprising a propargyl Claisen rearrangement, a [1,3]-H shift, a [1,7]-H shift (enolization), a 6π electrocyclization, and an aromatization reaction.
LiClO4-Promoted Addition of Alkyl Grignard and Alkynyllithium Reagents to Ketones. Comparison of a 5 M LiClO4/Diethyl Ether Solution with CeCl3
Ipaktschi, Junes,Eckert, Thomas
, p. 1171 - 1174 (2007/10/03)
The influence of a 5 M ethereal LiClO4 solution as solvent on the addition of different alkyl Grignard and alkynyllithium reagents to highly enolizable ketones was studied.A comparison with the results in the presence of CeCl3 shows a similar improvement in the yield. - Keywords: Nucleophilic addition; Lewis acid; Enolizable ketones; Alkyl Grignard; Alkynyllithium reagent
