54034-54-7Relevant articles and documents
Iodine Monoacetate for Efficient Oxyiodinations of Alkenes and Alkynes
Hokamp, Tobias,Storm, Alena Therese,Yusubov, Mekhman,Wirth, Thomas
supporting information, p. 415 - 418 (2017/10/30)
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.
Electrophilic Additions of Positive Iodine to Alkynes through an Iodonium Mechanism
Barluenga, Jose,Rodriguez, Miguel A.,Campos, Pedro J.
, p. 3104 - 3106 (2007/10/02)
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
Regio- and Stereo-selectivity of Acetoxymercuration of Acetylenes
Uemura, Sakae,Miyoshi, Haruo,Okano, Masaya
, p. 1098 - 1103 (2007/10/02)
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.