90331-52-5Relevant articles and documents
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.