140477-41-4Relevant academic research and scientific papers
Unusual oxidative cleavage of the aryl-ethynyl bonds in (arylethynyl)polymethylbenzenes with iodine in dimethyl sulfoxide
Yusubov,Zholobova,Filimonova,Vasil'eva,Filimonov,Chi, Ki-Whan
, p. 1051 - 1055 (2007/10/03)
While heating 1,2,4,5-tetramethyl-3,6-bis(phenylethynyl)benzene, 1,3,5-trimethyl-2,4-bis(phenylethynyl)benzene, and 1,2,4,5-tetramethyl-3-(phenylethynyl)benzene with iodine in DMSO in the absence of oxygen, the triple bonds are oxidized to give the corresponding 1,2-diketones. In the presence of oxygen, the previously unknown competitive oxidative process causes the cleavage of the aryl-ethynyl bonds so that duroquinone and the corresponding 4-hydroxybenzils are formed. This cleavage is produced by oxygen only in the presence of iodine and DMSO. It was shown that the key stage of the process is the formation of intermediate charge-transfer complexes between polymethylbenzene rings and iodine.
IODOSOARYL CARBOXYLATES IN ORGANIC SYNTHESIS. IV. SELECTIVE OXIDATION OF BIS- AND TRIS(PHENYLETHYNYL)ARENES BY IODOSOPHENYL TRIFLUOROACETATE
Karpitskaya, L. G.,Vasil'eva, V. P.,Merkushev, E. B.
, p. 1732 - 1736 (2007/10/02)
Bis- and tris(phenylethynyl) durene and mesitylene derivatives react with iodosophenyl trifluoroacetate via oxidation of one, two, or three triple bonds, depending on the amount of oxidizing agent used, to give the corresponding α-diketones.
