Abstract
A variety of ortho hydroxy substituted aromatic carbonyl compounds were regioselectively mono or diiodinated with iodine and iodic acid in excellent yields.
Highlights
Direct iodination methods have been intensively developed using iodinium donating systems, such as iodine nitrogen dioxide,[2] iodine-F-TEDA-[1-chloromethyl-4-fluoro1,4-diazoniabicyclo[2,2,2]octane-bis-(tetrafluoroborate)],3 bis-N-iodosuccinimide,[4] iodine-diiodine pentoxide,[5] mercury(II)-oxide-iodine,[6] iodine monochloride,[7] bis(pyridine)iodonium(I) tetrafluoroborate CF3SO3H,8 NIS-CF3SO3H,9 iodine silver sulfate,[10] iodine-mercury salts,[11] NaOCl-NaI,[12] iodine/Na2S2O813 and iodine-(NH4)[2] S2O8-CuCl2-Ag2SO4.14 Iodination of resorcinol derivatives and hydroxy chromones has been carried out using iodine and sodium hydroxide,[15] potassium iodide and potassium iodate[16] in acetic acid medium
A combination of iodine and iodic acid has been found to be an excellent reagent for the efficient iodination of aromatic carbonyl compounds such as hydroxy butyrophenones and hydroxy benzophenones
A variety of ortho hydroxy substituted aromatic carbonyl compounds were selected for the iodination reaction using iodine and iodic acid
Summary
Iodohydroxy aromatic ketones can be prepared by Fries rearrangement[1] of iodinated phenyl aromatic esters, after the Fries rearrangement, steam distillation is required to separate the isomers which is a time consuming method and iodophenols are not available.In recent years, direct iodination methods have been intensively developed using iodinium donating systems, such as iodine nitrogen dioxide,[2] iodine-F-TEDA-[1-chloromethyl-4-fluoro1,4-diazoniabicyclo[2,2,2]octane-bis-(tetrafluoroborate)],3 bis-N-iodosuccinimide,[4] iodine-diiodine pentoxide,[5] mercury(II)-oxide-iodine,[6] iodine monochloride,[7] bis(pyridine)iodonium(I) tetrafluoroborate CF3SO3H,8 NIS-CF3SO3H,9 iodine silver sulfate,[10] iodine-mercury salts,[11] NaOCl-NaI,[12] iodine/Na2S2O813 and iodine-(NH4)[2] S2O8-CuCl2-Ag2SO4.14 Iodination of resorcinol derivatives and hydroxy chromones has been carried out using iodine and sodium hydroxide,[15] potassium iodide and potassium iodate[16] in acetic acid medium. AOrganic Chemistry Synthesis Lab. Dnyanopasak College, Parbhani-431401, India. G. Department of Chemistry, Yeshwant Mahavidyalaya, Nanded-431 602, India. CDepartment of Chemistry, Shri Shivaji College, Parbhani-431401, India.
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