23264-13-3Relevant academic research and scientific papers
Silica gel-mediated hydrohalogenation of unactivated alkenes using hydrohalogenic acids under organic solvent-free conditions
Tanemura, Kiyoshi
supporting information, p. 4293 - 4298 (2018/11/10)
Silica gel-mediated hydrochlorination of unactivated alkenes using 35% hydrochloric acid under organic solvent-free conditions proceeded to give the corresponding chlorides in good yields. Hydrobromination or hydriodination using 47% hydrobromic acid or 55% hydriodic acid afforded the corresponding halides, respectively. Silica gel could be recycled five times without any significant loss of activities.
Synthesis of Ethers via Reaction of Carbanions and Monoperoxyacetals
Kyasa, ShivaKumar,Meier, Rebecca N.,Pardini, Ruth A.,Truttmann, Tristan K.,Kuwata, Keith T.,Dussault, Patrick H.
, p. 12100 - 12114 (2016/01/09)
Although transfer of electrophilic alkoxyl ("RO+") from organic peroxides to organometallics offers a complement to traditional methods for etherification, application has been limited by constraints associated with peroxide reactivity and stability. We now demonstrate that readily prepared tetrahydropyranyl monoperoxyacetals react with sp3 and sp2 organolithium and organomagnesium reagents to furnish moderate to high yields of ethers. The method is successfully applied to the synthesis of alkyl, alkenyl, aryl, heteroaryl, and cyclopropyl ethers, mixed O,O-acetals, and S,S,O-orthoesters. In contrast to reactions of dialkyl and alkyl/silyl peroxides, the displacements of monoperoxyacetals provide no evidence for alkoxy radical intermediates. At the same time, the high yields observed for transfer of primary, secondary, or tertiary alkoxides, the latter involving attack on neopentyl oxygen, are inconsistent with an SN2 mechanism. Theoretical studies suggest a mechanism involving Lewis acid promoted insertion of organometallics into the O-O bond.
Polyvinylpyrrolidone-bromine complex: An efficient polymeric reagent for selective preparation of benzyl bromides in the presence of hexamethyldisilane
Mokhtary, Masoud,Lakouraj, Moslem M.
, p. 305 - 309 (2012/10/29)
Benzylic bromides were conveniently obtained in high yields via the reaction of the corresponding alcohols with crosslinked polyvinylpyrrolidone- bromine complex (PVPP-Br2)/hexamethyldisilane in chloroform at reflux condition. Selective conversion of benzyl alcohol to benzyl bromide in the presence of primary aliphatic alcohols, e.g. 2-phenylethanol was also achieved.
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.
Catalytic activity of K10-montmorillonite in reaction of arenes with some mono- and di-functional alkylating agents, mostly derived from isobutane and isobutene
Albar,Basaif,Khalaf, Ali A.
, p. 161 - 166 (2007/10/03)
K10-montmorillonite has been tested as Friedel-Crafts catalyst in the alkylation of benzene, toluene and anisole with one or more of the alkylating agents 1-10. The reaction products consisted essentially of 1,1- and 1,2-diaryl-2-methylpropane derivatives (e.g. 11 and 12 respectively) together with side products resulting from transalkylation, monoalkylation, hvdride transfer and elimination. K 10-montmorillonite has also been used to catalyse the alkylation of naphthalene with benzyl alcohol whereby a mixture of α-and β-benzylnaphthalene is obtained. The results, explained in terms of carbocation transformations, show K 10-montmorillonite to be a mild catalyst with no subsequent side-chain isomerising ability just like FeCl3, AlCl3-CH3NO2, TiCl4 and ZrCl4.
