69381-33-5Relevant academic research and scientific papers
Halogen and chalcogen cation pools stabilized by DMSO. Versatile reagents for alkene difunctionalization
Ashikari, Yosuke,Shimizu, Akihiro,Nokami, Toshiki,Yoshida, Jun-Ichi
supporting information, p. 16070 - 16073 (2013/11/19)
Halogen and chalcogen cations (X+ = Br+, I +, ArS+, and ArSe+) were generated by low-temperature electrochemical oxidation in the presence of dimethyl sulfoxide (DMSO) and were accumulated in the solution. DFT calculations indicated that DMSO stabilizes these cations by coordination. The complexes of I+ with one and two DMSO molecules were observed by cold-spray-ionization MS analyses. The stability of the resulting cation pools of X+ increased in the order of Br+ + + +, which could be explained in terms of the electronegativity of X. The cation pools served as versatile reagents for organic synthesis; the reactions with alkenes gave β-X-substituted alkoxysulfonium ions, which were converted to the corresponding carbonyl compounds by the treatment with triethylamine, whereas the treatment with methanol gave the corresponding alcohols. The reactions with aminoalkenes and 1,6-dienes gave the cyclized products.
Reaction of enol ethers with the I2-H2O2 system: Synthesis of 2-iodo-1-methoxy hydroperoxides and their deperoxidation and demethoxylation to 2-iodo ketones
Terent'ev, Alexander O.,Borisov, Alexander M.,Platonov, Maxim M.,Starikova, Zoya A.,Chernyshev, Vladimir V.,Nikishin, Gennady I.
experimental part, p. 4159 - 4166 (2011/03/18)
The reaction of enol ethers with the I2-H2O 2 system in diethyl ether affords 2-iodo ketones and the previously unknown 2-iodo-1-methoxy hydroperoxides. In the presence of the I 2-H2O2 system, the latter compounds undergo deperoxidation and demethoxylation to form 2-iodo ketones. The reaction conditions were found for the synthesis of 2-iodo ketones from enol ethers in 67-94% yields. Georg Thieme Verlag Stuttgart - New York.
ONE POT SYNTHESIS OF α-BROMO AND α-IODO KETONES FROM EPOXIDES
Denis, J. N.,Krief, A.
, p. 1429 - 1430 (2007/10/02)
α-bromo and α-iodo ketones are obtained in good yield and in one pot by reaction of terminal and disubstituted epoxides with trimthylsilyl halides and further oxidation (CrO3/H2SO4).
Reaction of Enol Silyl Ethers with Silver Carboxylate-Iodine. Synthesis of α-Acyloxy Carbonyl Compounds
Rubottom, George M.,Mott, Robert C.,Juve, Henrik D.
, p. 2717 - 2721 (2007/10/02)
The sequential treatment of enol silyl ethers with silver carboxylate-iodine (2:1) and then fluoride affords high yields of the corresponding α-acyloxy carbonyl compounds.Thus a wide range of variation is now possible for the acyloxy portion of the molecu
