90331-51-4Relevant academic research and scientific papers
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.
PARTICIPATION OF SULFONATE IONS IN THE ELECTROPHILIC ADDITION OF HALOGENS TO OLEFINS
Zefirov, N. S.,Koz'min, A. S.,Dan'kov, Yu. V.,Zhdankin, V. V.,Kirin, V. N.
, p. 205 - 213 (2007/10/02)
The reactions of ethylene, 1-heptene, cyclohexene, and styrene with chlorine and bromine in methylene chloride and chloroform in the presence of tetrabutylammonium p-toluenesulfonate and tetrabutylammonium methanesulfonate were investigated.In all cases the 2-halogenoalkyl esters of the sulfonic acids were obtained with comparable yields in addition to the 1,2-dihalides.The addition of chlorine and bromine to cyclohexene and also of bromine to 1-heptene in acetic acid in the presence of lithium p-nitrobenzenesulfonate leads to 2-halogenoalkyl esters of the sulfonicacids and acetic acid in addition to the 1,2-dihalides.These data indicate concurrent combination of the sulfonate anions at the concluding stage of AdE reactions.The mechanistic aspects and consequences of this effect are discussed.
