120385-80-0Relevant academic research and scientific papers
Regioselective Diboron-Mediated Semireduction of Terminal Allenes
Gates, Ashley M.,Santos, Webster L.
supporting information, p. 4619 - 4624 (2019/12/11)
A method for the regioselective reduction of the terminal double bond of 1,1-disubstituted allenes has been developed. In the presence of a palladium catalyst, tetrahydroxydiboron and stoichiometric water, allene semireduction proceeds in high yield to afford Z-alkenes selectively.
Catalytic C-F bond activation of geminal difluorocyclopropanes by nickel(i) complexes via a radical mechanism
Wenz, Jan,Rettenmeier, Christoph A.,Wadepohl, Hubert,Gade, Lutz H.
supporting information, p. 202 - 205 (2015/12/26)
Nickel(ii) fluorido complexes bearing NNN-pincer ligands were found to be catalysts in the hydrodefluorination of geminal difluorocyclopropanes which undergo ring-opening to form the corresponding monofluoroalkenes in good yield and high Z-selectivities. Evidence for a radical based mechanism involving nickel(i) and nickel hydrido complexes as key intermediates was obtained in the corresponding stoichiometric reactions.
Synthesis of terminal allenes through copper-mediated cross-coupling of ethyne with N-tosylhydrazones or α-diazoesters
Ye, Fei,Wang, Chengpeng,Ma, Xiaoshen,Hossain, Mohammad Lokman,Xia, Ying,Zhang, Yan,Wang, Jianbo
, p. 647 - 652 (2016/09/12)
Ethyne is employed as coupling partner in coppermediated cross-coupling reactions with N-tosylhydrazones and α-diazoacetate, leading to the development of a new synthetic method for terminal allenes. With this novel coupling method, the terminal allenes w
Photocyclization between Quinones and Allenes via Photoinduced Electron Transfer
Maruyama, Kazuhiro,Imahori, Hiroshi
, p. 2692 - 2702 (2007/10/02)
Photochemical reactions of halo-1,4-naphthoquinones with 1,1-diphenylallenes afforded spiropyran adducts derived from cycloaddition between carbonyl group of quinone and allene in good yield.In the photoreactions of 2,3-dichloro-1,4-naphthoquinone with monophenylallenes, cycloadducts were obtained in addition to spiropyran derivatives.Considering the relationship between formation of spiropyran adducts and the free energy changes (ΔG) together with substituent effects, solvent effects, and CIDNP (chemically induced dynamic nuclear polarization), we propose an electron-transfer mechanism.That is, radical ion pair formation from excited triplet quinone and allene is followed by conversion to a biradical.Subsequent bond formation between the ketyl radical in quinone moiety and ortho position of the phenyl substituents on the allene skeleton leads to the spiropyran adduct after subsequent 1,5-hydrogen shift.
