100608-25-1Relevant articles and documents
Addition of Acyl and Sulfonyl Hypohalites Generated from N-Halogeno Amides to Alkenes: Synthesis of trans-vic-Halogeno Esters and their Conversion to cis-1,2-Diols
Goosen, Andre,Hoffman, Eric,Taljaard, Benjamin
, p. 41 - 44 (2007/10/02)
N-Iodo- and N-bromo-p-nitrobenzamide have been shown to react with various organic acids to form the respective acyl or sulfonyl hypoiodites or hypobromites.These readily add to double bonds under mild conditions to yield trans-vic-halogeno esters.The ste
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.