50895-58-4Relevant articles and documents
Cyclopropylidene Radical Anion and 1,4-Elimination-Type Remote Ionization Effect in the Reduction of Bi(gem-dihalocyclopropane) Systems
Oku, Akira,Tsuji, Hideo,Yoshida, Mitsuhiro,Yoshiura, Naoto
, p. 1244 - 1246 (1981)
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REACTIONS OF DIAZOALKANES WITH UNSATURATED COMPOUNDS. 6. CATALYTIC CYCLOPROPANATION OF UNSATURATED HYDROCARBONS AND THEIR DERIVATIVES WITH DIAZOMETHANE
Dzhemilev, U. M.,Dokichev, V. A.,Sultanov, S. Z.,Khusnutdinov, R. I.,Tomilov, Yu. V.,et al.
, p. 1707 - 1714 (2007/10/02)
A systematic study has been conducted of the catalytic reaction of diazomethane with cyclic and polycyclic unsaturated hydrocarbons, conjugated dienes, as well as with a series of functionalized unsaturated conpounds.The feasibility of using transition metal, nontransition metal, and rare earth metal compounds of, for example, Co, Ni, Zr, Rh, and Dy, has been demonstrated for the first time.It has also been established that Pd(acac)2 has very high activity as a catalyst for the cyclopropanation of terminal and endocyclic double bonds by diazomethane, and that its activity is reduced upon the introduction of n-donor ligands or in the presence of strong polar solvents.
Nonhomogeneous Phase Effect on the Generation of Carbene Radical Anions in the Birch-Type Reduction of Bis(gem-dihalocyclopropyl) Compounds
Oku, Akira,Yoshiura, Naoto,Okuda, Tomohisa
, p. 617 - 619 (2007/10/02)
The reduction of 1,2-bis(gem-dichlorocyclopropyl)ethane (5) with sodium metal (4 molar equiv with respect to 5) in a mixed solution of NH3-THF-EtOH, which separated a metallic liquid phase on mixing, gave the parent hydrocarbon product predominantly.On the other hand, analogous reduction of 5 with lithium metal, which produced a homogeneous colored solution, predominantly gave the di- and trichloro intermediate products.The unusual results of the reduction with a nonhomogeneous reductant mixture are explained in terms of a rapid and consecutive electron transfer tothe molecule which is taken into or located in the vicinity of the reductant phase. 3,3,8,8-Tetrachlorotricyclo2,4>octane behaved analogously.