13151-27-4Relevant articles and documents
Zirconocene-catalyzed alkylative dimerization of 2-methylene-1,3-dithiane via a single electron transfer process to provide symmetrical vic-bis(dithiane)s
Yoshida, Suguru,Yorimitsu, Hideki,Oshima, Koichiro
, p. 3110 - 3114 (2007)
A mixture of tertiary alkyl halide and 2-methylene-1,3-dithiane was treated with butylmagnesium bromide in the presence of a catalytic amount of zirconocene dichloride. The reaction resulted in alkylative dimerization to yield the corresponding vic-bis(dithiane). The reaction would proceed as follows. A single electron transfer from low-valent zirconocene to alkyl halide would generate the corresponding alkyl radical. The radical adds to 2-methylene-1,3-dithiane to afford the corresponding radical stabilized by the two sulfur atoms. A couple of the stable radicals finally undergo dimerization.
Silver-catalyzed benzylation and allylation of tertiary alkyl bromides with organozinc reagents
Mitamura, Yukihiro,Asada, Yoshihiro,Murakami, Kei,Someya, Hidenori,Yorimitsu, Hideki,Oshima, Koichiro
experimental part, p. 1487 - 1493 (2011/07/07)
Silver salts catalyze the benzylation and allylation of tertiary alkyl bromides with organozinc reagents. The reactions create quaternary carbon centers efficiently. Treatment of gem-dibromoalkanes with benzylic or allylic zinc reagents under silver catalysis leads to dibenzylation or diallylation. The functional-group compatibility of the present reactions is wider than that of the previous reactions with Grignard reagents.
THE TITANOCENE METHYLENE-ZINC HALIDE COMPLEX: A CONVENIENT SYNTHESIS AND ITS METHYLENATING ACTION ON UNSATURATED CARBON CENTERS
Eisch, John J.,Piotrowski, Andrzej
, p. 2043 - 2046 (2007/10/02)
The titanocene methylene-zinc halide complex, which can be conveniently prepared by treating titanocene dichloride with methylenezinc iodide in THF solution, readily methylenates ketones, nitriles, and alkynes.
New Synthesis of Cyclopropanes from 1,3-Dicarbonyl Compounds Utilizing Electroreduction of 1,3-Dimethanesulfonates
Shono, Tatsuyo,Matsumura, Yoshihiro,Tsubata, Kenji,Sugihara, Yoshihiro
, p. 3090 - 3094 (2007/10/02)
Electroorganic synthesis of cyclopropanes from dimethanesulfonates of 1,3-diols is described.The process involves reduction of 1,3-dicarbonyl compounds with LiAlH followed by esterification with methanesulfonyl chloride and electroreduction.