27304-57-0Relevant academic research and scientific papers
BROMO- AND IODOFUNCTIONALIZATION OF OLEFINS BY MEANS OF THE MERCURY(II) SALT-HALOGEN COMBINATION
Barluenga, Jose,Martinez-Gallo, Jose M.,Najera, Carmen,Yus, Miguel
, p. 2416 - 2443 (2007/10/02)
Mercury(II) salts (fluoride, chloride, bromide, formate, acetate, trifluoroacetate, propionate, benzoate, nitrate, methanesulphonate, toluene-p-sulphonate, thiocyanate, and toluene-p-sulphinate) reacted with monoolefines and bromine or iodine to give 1,2-bifunctionalized products resulting from the addition of the halogen and the mercury(II) salt anion selectively.The addition was regiospecific for styrene and for 3,3-dimethylbut-1-ene affording Markownikoff type products, respectively.In the case of hex-1-ene both regioisomers were obtained.For cyclic alkenes trans-1,2-derivatives were stereoselectively obtained.Cycloocta-1,5-diene gave the monoaddition products.Buta-1,3-diene underwent mainly 1,2-addition and allylic derivatives gave the corresponding 1,2,3-trifunctionalized compounds.A possible ionic mechanism is proposed to explain the obtained addition products.
The Mercury(II) Salt-Halogen Combination HgX2-Hal2: A Versatile Reagent for Stereoselective Addition of Hal-X to Alkenes
Barluenga, Jose,Martinez-Gallo, Jose M.,Najera, Carmen,Yus, Miguel
, p. 1422 - 1423 (2007/10/02)
The reaction of mercury(II) salts (fluoride, chloride, bromide, nitrate, methanesulphonate, toluene-p-sulphinate, and toluene-p-sulphonate) and halogens (bromine or iodine) with alkenes leads to the corresponding 1,2-bifunctionalized products resulting fr
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.
