69180-49-0

Basic information

• Product Name: bis(acetyloxy)(2-methoxyphenyl)-lambda~3~-iodane
• CAS NO: 69180-49-0
• Molecular Formula: C₁₁H₁₃IO₅
• Molecular Weight: 352.1224
• Mol File: 69180-49-0.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: bis(acetyloxy)(2-methoxyphenyl)-lambda~3~-iodane(CAS DataBase Reference)
• NIST Chemistry Reference: bis(acetyloxy)(2-methoxyphenyl)-lambda~3~-iodane(69180-49-0)
• EPA Substance Registry System: bis(acetyloxy)(2-methoxyphenyl)-lambda~3~-iodane(69180-49-0)

Safety Data

• Hazardous Substances Data: 69180-49-0(Hazardous Substances Data)

Upstream product

• 79-21-0 peracetic acid 
• 529-28-2 4-iodoanisol 
• 108-24-7 acetic anhydride 
• 2754-27-0 trimethylsilyl acetate 
• 533-58-4 2-Iodophenol 
• 64-19-7 acetic acid 

Downstream Products

• 1222532-02-6 bis(2-methoxyphenyl)iodonium tosylate 
• 1379474-24-4 dimethyl 2-((2-methoxyphenyl)-λ³-iodanylidene)malonate 

Relevant articles and documents

N -Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts to Generate α,β-Unsaturated Ketones

An organocatalyzed metal-free, direct olefination of aldehydes with vinyliodonium salts has been achieved by an N-heterocyclic carbene-promoted C-H bond activation. The reaction proceeds under very mild conditions, delivering a range of (hetero)aryl-vinyl ketones in good yields. The retention of the double bond configuration is uniformly observed, and the application of 2-methoxyphenyl auxiliary group in iodonium salts secures a complete selectivity of the vinyl transfer.

Generation of Aryl Radicals through Reduction of Hypervalent Iodine(III) Compounds with TEMPONa: Radical Alkene Oxyarylation

A novel method for selective generation of aryl radicals from diaryliodonium salts and iodanylidene malonates with sodium 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPONa) as a single-electron transfer (SET) reducing reagent is described. In the presence of various alkenes, aryl radicals formed after SET-reduction of hypervalent iodine compounds undergo alkene addition and the adduct radicals that are thus generated are efficiently trapped by the concomitantly generated TEMPO radical to eventually afford oxyarylated products in moderate to very good yields. The efficiency of aryl radical generation of various iodine(III) reagents is studied and the generation of an iodanylidene malonate aryl radical is also investigated by computational methods.

Synthesis of ionic-liquid-supported diaryliodonium salts

The synthesis of ionic-liquid-supported diaryliodonium salts is described. The synthesis is simple and practical, and the ionic liquid products require no chromatographic purification. The ionic-liquid-supported diaryliodonium salts are quite stable, and they did not show any sign of decomposition or loss of reactivity, even after being stored for one month at 5 °C. The reactivity of these salts was explored in the phenylation of substituted phenols and carboxylic acids, and the corresponding diaryl ethers and aryl esters, respectively, were synthesized in good to excellent yields and with high purities.