54034-54-7

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 1600-27-7 mercury(II) diacetate 
• 64-19-7 acetic acid 
• 6540-76-7 iodine monoacetate 

Relevant academic research and scientific papers

Iodine Monoacetate for Efficient Oxyiodinations of Alkenes and Alkynes

A novel and inexpensive, environmentally friendly method for the preparation of iodine monoacetate is presented using iodine and Oxone in acetic acid/acetic anhydride. The reagent is used in a highly efficient approach for the regio- and diastereoselective iodo-acetoxylation of alkenes and alkynes in a simple one-pot process.

Reactions of alkynes with iodine and potassium iodide in acetic acid in the presence of nitrates. Simple synthesis of 1-iodo-2-nitroalkenes

Terminal and internal alkynes react with I2 or KI and nitrates in acetic acid under mild conditions to give the corresponding 1-iodo-2-nitroalkenes as the major products. The effect of the reactant nature and reaction conditions on the yield of products was studied. Oxygen was found to play an important role in the formation of the target products. A possible mechanism of the reaction includes a series of redox transformations of I2 or I- and NO-3 to form INO2 which then adds to alkynes by a radical path. In reactions with potassium iodide, oxygen acts as an additional oxidant which converts NO into active nitrogen dioxide.

Electrophilic Additions of Positive Iodine to Alkynes through an Iodonium Mechanism

Alkynes react with bis(pyridine)iodonium (I) tetrafluoroborate (1) and nucleophiles (CH3COOH, HCOOH, Cl-, pyridine, Br-, I-) to give 1,2 iodofunctionalized alkenes.The regiochemistry of the processes is in accordance with

Stereoselective Bifunctionalization of Alkynes by Means of the Mercury(II) Salt-Iodine Combination

The reaction of alkynes with iodine and mercury(II) salts (chloride, acetate, methanesulphonate, toluene-p-sulphonate, benzylsulphide, toluene-p-sulphinate, and thiocyanate) affords stereoselectively E-β-functionalized vinyl iodides resulting from the ionic addition of iodine and the mercury(II) salt anion.Unsymmetrical alkynes yield regiospecifically Markovnikov addition products.In the case of mercury(II) thiocyanate the reaction can be used also for the stereoselective preparation of E-1,2-dithiocyanatoalkenes.An ionic mechanism is proposed according to the observed regio- and stereochemistry.

Regio- and Stereo-selectivity of Acetoxymercuration of Acetylenes

Acetoxymercuration of alkylphenylacetylenes (PhCCR; R = Me, Et, Prn, or Bun) (1) in acetic acid at 20 - 60 deg C proceeds completely in a trans-fashion to afford a regioisomeric mixture of two vinylmercury(II) compounds, Ph(OAc)C=C(HgCl)R (2) and Ph(HgCl)C=C(OAc)R (3), the extent of attack of Hg at the carbon α to alkyl group to form (2) being increased upon increasing the carbonyl chain length of the alkyl group .A bridged mercurinium ion intermediate in which phenyl and alkyl groups are bent toward the attacking side of acetate anion is proposed for explaining a marked dependence of the isomer ratio (2):(3) on the kind of alkyl groups.Similar treatment of diphenylacetylene at 20 - 95 deg C gives only the cis-adduct as reported previously, while that of diethyl-acetylene affords the trans-adduct and a mixture of trans- and cis-adduct at 20 deg C and at 65 deg C, respectively.The NaBH4 reduction of (2, R = Me) in neutral condition produces a mixture of (Z)- and (E)-1-acetoxy-1-phenylpropene (ca. 3-5:1) in contrast to the reduction of thallium analogue of (2) which gives only the Z-isomer.