24168-52-3Relevant academic research and scientific papers
REACTION OF 1,1-DIFLUOROCYCLOPROPANES WITH ORGANOLITHIUM COMPOUNDS
Suda, Minoru
, p. 4355 - 4358 (1980)
Substitued 1,1-difluorocyclopropanes react with organolithium reagents to provide either cyclopropenes or mono-substitued acetylenes depending upon the substitution patterns.
Selective Alkynylallylation of the C?C σ Bond of Cyclopropenes
Chen, Ying-Chun,Jiang, Zeqi,Niu, Sheng-Li,Ouyang, Qin,Xiao, Qing,Zeng, Qiang
supporting information, p. 297 - 303 (2020/11/30)
A Pd-catalyzed regio- and stereoselective alkynylallylation of a specific C?C σ bond in cyclopropenes, using allyl propiolates as both allylation and alkynylation reagents, has been achieved for the first time. By merging selective C(sp2)-C(sp3) bond scission with conjunctive cross-couplings, this decarboxylative reorganization reaction features fascinating atom and step economy and provides an efficient approach to highly functionalized dienynes from readily available substrates. Without further optimization, gram-scale products can be easily obtained by such a simple, neutral, and low-cost catalytic system with high TONs. DFT calculations afford a rationale toward the formation of the products and indicate that the selective insertion of the double bond of cyclopropenes into the C-Pd bond of ambidentate Pd complex and the subsequent nonclassical β-C elimination promoted by 1,4-palladium migration are critical for the success of the reaction.
Rearrangement of cyclopropylborane into boretane
Rubina, M.,Rubin, M.
, p. 807 - 821,15 (2020/09/09)
Previously unknown boron-containing four-membered unsaturated heterocycle boretane was obtained via novel thermal rearrangement of cyclopropylborane and investigated by NMR and IR spectroscopy. Formation of boretane was also confirmed through its chemical
ZINC-PROMOTED REACTIONS. III. THE REDUCTION OF α,β-UNSATURATED KETONES IN ACETIC ACID
Vona, Maria Luisa Di,Rosnati, Vittorio
, p. 25 - 29 (2007/10/02)
The zinc-promoted reduction of 1,3-diphenylpropenone, 1, 4-phenyl-3-buten-2-one, 2, and 3-penten-2-one, 3, have been reinvestigated in AcOH.The reduction of 1 in neat AcOH gave 1,3-diphenylpropene, 4, 1,3-diphenylpropan-1-ol, 5, 1,3-diphenylpropane, 6, and 1,3,4,6-tetraphenylhexane-1,6-dione, 12, in comparable yields, accounting for about 90percent of the product.In the presence of co-reagents like LiCl, HCl, and CF3CO2H, the predominant products was 4, and a more scattered product distribution was observed.In addition to compounds 4-6, and 12, 1-acetoxy-1,2-diphenylcyclopropane, 1,2-diphenylcyclopropene, 1,2,4,5-tetraphenylbenzene, and two dimeric polyenes were formed in minor amounts.Instead, the reduction of 2 gave ketonic compounds only, 4-phenylbutan-2-one, being the predominant product in all the reactions performed in anhydrous AcOH.Under the classical Clemmensen procedure, i.e. in 7 M HCl, the reductions of 1 and 2 were diverted towards the formation of dimeric ketones.The reduction of 3 resulted exclusively in the saturation of the double bond.The mechanisms possibly involved and, in particular, the chemoselective reduction of the carbon-carbon double bond, are discussed.
