40441-35-8Relevant academic research and scientific papers
Photocycloaddition of chloromethyl alkenyl ketones with olefins in the presence of silver trifluoromethanesulfonate
Sawayanagi, Yukihiro,Sato, Tadashi,Shimizu, Isao
, p. 843 - 844 (1997)
The photoreaction of chloromethyl alkenyl ketones with olefins in the presence of AgOTf proceeded to give five or six membered cyclic compounds.
Influence of tetrahydrofuran on reactivity, aggregation, and aggregate structure of dimethylcuprates in diethyl ether
Henze, Wolfram,Vyater, Armand,Krause, Norbert,Gschwind, Ruth M.
, p. 17335 - 17342 (2005)
The comprehension of factors influencing the reactivity of organocuprates is still far from enabling a rational control of their reactions. Especially the degree of aggregation and structures of organocuprates are the focus of discussion about the factors affecting their reactivity. Therefore, this study combines kinetic measurements and NMR investigations to elucidate the influence of disaggregation via addition of tetrahydrofuran (THF) on the reactivity and aggregate structure of Gilman cuprates. As model systems, Me2CuLi-Lil (1-Lil) and Me2CuLi-LiCN (1-LiCN) in diethyl ether (DEE) were chosen; as model reaction, the 1,4-addition to 4,4-dimethylcyclohex-2-enone. The kinetic data show for 1-Lil a pronounced acceleration effect upon addition of distinct amounts of THF, whereas the reactivity of 1-LiCN continuously decreases with the addition of THF. Series of NMR diffusion measurements as well as 1H-7Li heteronuclear Overhauser effect (HOE), and 1H-1H nuclear Overhauser effect (NOE) spectra show different structural influences of THF on 1-Lil and 1-LiCN. For 1-Lil, small salt units are separated from the cuprate aggregate by THF. In contrast to this, THF disaggregates the oligomeric structures of 1-LiCN, while the core structures remain intact with salt attached. Thus, the reactivity of 1-Lil seems to be fine-tuned through distinct amounts of salt or THF, whereas the decreasing reactivity of 1-LiCN correlates with the disaggregation of oligomers via THF. Thus, for synthetic chemists with reactivity problems in specific reactions of iododialkylcuprates, the addition of small amounts of THF might be useful to enhance the reactivity. In addition to these structure-reactivity studies, the CN- group is shown to be directly attached to the cuprate moiety via a combination of 1H-13C HOE- and 1H-1H NOEs. This represents the first direct experimental evidence in solution for the position of the CN- group relative to the cuprate moiety in cyano-Gilman cuprates.
A metal nanoparticle-based supramolecular approach for aqueous biphasic reactions
Mhadgut, Shilpa C.,Palaniappan, Kumaranand,Thimmaiah, Muralidhara,Hackney, Stephen A.,Toeroek, Bela,Liu, Jian
, p. 3207 - 3209 (2007/10/03)
β-cyclodextrin immobilized on Pd nanoparticles was successfully employed as an efficient phase-transfer catalyst in aqueous biphasic hydrogenation reactions. The Royal Society of Chemistry 2005.
Functional Group Hybrids. Reactivity of α'-Nucleofuge α,β-Unsaturated Ketones. 1. Reactions with Organocopper Reagents
Barbee, Thomas R.,Albizati, Kim F.
, p. 6764 - 6773 (2007/10/02)
A series of α-nucleofuge α',β'-unsaturated ketones encompassing a variety of structural types and nucleofuges was prepared.Treatment of these compounds with lithium dimethylcuprate or methylcopper leads primarily to either reductive cleavage of the α-nucl
Regio- and Stereoselectivity of the Hydrocarbonylating Cyclization of 1,4-Dienes with Carbon Monoxide: Synthesis of (+/-)-(α)-Cuparenone
Eilbracht, Peter,Balss, Erika,Acker, Michael
, p. 825 - 839 (2007/10/02)
Directed towards the synthesis of the cuparene skeleton the hydrocarbonylating cyclization of 1,4-dienes 16, 27 to form cyclopentanones 17, 28 was tested for its regio- and stereoselectivity as well as the toleration of aryl groups in this cyclization met
