20421-40-3Relevant academic research and scientific papers
Reaction of alkylhypochlorites and xenon difluoride with cyclohexene
Shellhamer,Horney,Toth,Heasley
, p. 6903 - 6906 (2007/10/02)
Reactions of alkylhypochlorites and xenon difluoride with cyclohexene give primarily 1-chloro-2-fluorocyclohexanes via formation of a complex between xenon difluoride and the alkylhypochlorite.
OXIDATIVE ADDITION OF ANIONS TO ALKENES BY THE ACTION OF COMPOUNDS OF TETRAVALENT LEAD IN THE PRESENCE OF CHLORIDE ION IN AN ACIDIC MEDIUM
Serguchev, Yu. A.,Gutsulyak, R. B.
, p. 1784 - 1790 (2007/10/02)
In the reaction of alkenes (cyclohexene, 1-hexene, styrene) with compounds of tetravalent lead in various acids (trifluoroacetic, acetic, methanesulfonic, perchloric) in the presence of metal chlorides the joint addition of the chloride anion and the anion of the respective acids to the alkenes takes place with a high degree of selectivity, leading to the formation of vicinal bifunctional derivatives of alkanes.The effectiveness of the addition of the anions of the acids to the alkenes under the given conditions varies directly with the strength of the acid and inversely with the nucleophilicity and the basicity of its anion.A new convenient method is proposed for the oxidative chlorofluorination of cyclohexene in aqueous hydrofluoric acid.
Efficient Utilization of Tetrabutylammonium Bifluoride in Halofluorination Reactions
Camps, F.,Chamorro, E.,Gasol, V.,Guerrero, A.
, p. 4294 - 4298 (2007/10/02)
The halofluorination reaction of a variety of alkenes by using tetrabutylammonium bifluoride (TBABF) in the presence of N-halosuccinimide is described.This process occurs stereospecifically to afford anti addition products, and with unsymmetrical olefins a marked Markovnikov-type regioselectivity is observed.In some cases, formation of a remarkable amount of the corresponding dihalo derivatives was found, but this undesirable side reaction can be avoided by using N-iodosucciniumide (NIS) as halogenating agent.If N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS) is utilized, these dihalo compounds can be easily removed from the halofluorinated compounds by simple column chromatography on silica gel.A mechanism for this side reaction is postulated.
BORON TRIFLUORIDE PROMOTED REACTIONS OF N-HALOELECTROPHILES WITH ALKENES
Heasley, Gene E.,Janes, J. Mark,Stark, Stephen R.,Robinson, Brian L.,Heasley, Victor L.,Shellhamer, Dale F.
, p. 1811 - 1814 (2007/10/02)
N-Haloelectrophiles react with alkenes in the presence of boron trifluoride etherate to give halofluorides and N-halo adducts.
Boron Trifluoride Promoted Reaction of Alkyl Hypohalites with Alkenes. A New Synthesis of Fluoro Halides
Heasley, Victor L.,Gipe, Robert K.,Martin, Jody L.,Wiese, Harry C.,Oakes, Melanie L.,Shellhamer, Dale F.
, p. 3195 - 3199 (2007/10/02)
The reactions of the following alkenes with alkyl hypohalites and boron trifluoride (BF3) were investigated: cyclohexene (3), 1-hexene (8), trans-1,2-dichloroethylene (15), methyl acrylate (18), methyl crotonate (25), methyl isocrotonate (29), butadiene (33), methyl vinyl ketone (42), and styrene (45).Reactions of these alkenes with methyl hypochlorite (1) and BF3 in dichloromethane give fluoro chloride adducts as well as methoxy chlorides with the percentage of fluoro chlorides varying from 75percent for 29 to 8percent for 45.Fluoro bromide adducts are obtained with methyl hypobromite (2).Reactions with the tert-butyl hypohalites and BF3 also give fluoride incorporation.The percentage of fluoride incorporation with 1 or 2 is significantly greater in carbon tetrachloride than in dichloromethane.
