105174-52-5Relevant academic research and scientific papers
Aerobic oxidative α-iodination of carbonyl compounds using molecular iodine activated by a nitrate-based catalytic system
Prebil, Rok,Stavber, Stojan
, p. 5643 - 5647 (2014)
The novel reaction system comprising air/NH4NO3(cat.)/I2/H2SO4(cat.)is introduced as a simple, safe, cheap, efficient, and regioselective mediator for direct aerobic oxidative α-iodination of aryl, heteroaryl, alkyl, and cycloalkyl methyl ketones. The reaction system enabled the moderate to quantitative regioselective iodination of a large range of different methyl ketone derivatives including those bearing oxidizable heteroatom (S, N) substituents. Several activated aromatic compounds were also efficiently and selectively iodinated. The practical applicability of the presented reaction system was shown on 20 mmol scale under ambient pressure and 100% conversion of substrate was achieved.
Synthesis of Phenolic Ketones, an Ester Ketone of Guaiacol, and a Ketone of Veratrole Containing Chlorine, Bromine, or Iodine in the Side-chain
Kossmehl, Gerhard,Frohberg, Hans-Christian
, p. 50 - 64 (2007/10/02)
The ω-bromo and ω-chloro ketones 1-8, 10-14 of phenols as well as the ω-bromo ketone 9 of veratrole are synthesized according to the Friedel-Crafts acylation (FCA) using different variations and specific reaction conditions.Under these conditions hydroquinone furnishes the esters of the ω-bromo- and ω-chlorocarboxylic acids 28-31, whereas phloroglucinol does not result in defined reaction products.Guaiacol yields 16 with an ester as well as a ketone group at its aromatic nucleus.Bromination of 3',4'-dihydroxyisobutyrophenone with CuBr2 leads to 2-bromo-3',4'-dihydroxyisobutyrophenone (15).The ω-iodo ketones 17-27 of phenols and their methyl ethers have been obtained from the corresponding ω-bromo or ω-chloro ketone on treatment with NaI in acetone.
