34107-52-3

Basic information

• Product Name: Iodonium, phenyl-, 2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylide
• CAS NO: 34107-52-3
• Molecular Formula: C12H11IO4
• Molecular Weight: 346.121
• Mol File: 34107-52-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Iodonium, phenyl-, 2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylide(CAS DataBase Reference)
• NIST Chemistry Reference: Iodonium, phenyl-, 2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylide(34107-52-3)
• EPA Substance Registry System: Iodonium, phenyl-, 2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylide(34107-52-3)

Safety Data

• Hazardous Substances Data: 34107-52-3(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 2033-24-1 cycl-isopropylidene malonate 
• 536-80-1 iodosylbenzene 
• 3240-34-4 [bis(acetoxy)iodo]benzene 

Downstream Products

• 86001-87-8 2,2-Dimethyl-5-(triphenyl-λ⁵-arsanylidene)-[1,3]dioxane-4,6-dione 
• 1393841-64-9 1-(1,2-diphenylethoxy)-2,2,6,6-tetramethylpiperidine 
• 3709-33-9 1-benzyl-6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione 
• 6258-48-6 6,6-dimethyl-1-(4-nitrophenyl)-5,7-dioxaspiro[2.5]octane-4,8-dione 
• 97381-37-8 1-(4-fluorophenyl)-6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione 

Relevant articles and documents

Blue LED Irradiation of Iodonium Ylides Gives Diradical Intermediates for Efficient Metal-free Cyclopropanation with Alkenes

A facile and highly chemoselective synthesis of doubly activated cyclopropanes is reported where mixtures of alkenes and β-dicarbonyl-derived iodonium ylides are irradiated with light from blue LEDs. This metal-free synthesis gives cyclopropanes in yields

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.

Simplified synthesis of aryliodonium ylides by a one-pot procedure

A simplified synthesis of iodonium ylides was developed by the one-pot synthesis of phenyliodonium-(5-[2,2-dimethyl-1,3-dioxane-4,6-dione]) ylide as a model system. Such ylides are excellent precursors for nucleophilic no-carrier-added 18F-fluorination of even non-activated arenes. The suitability of the one-pot method is exemplified for several electron rich iodonium ylides. Further, the syntheses of 2-, 3- and 4-bromophenyliodonium-(5- [2,2-dimethyl-1,3-dioxane-4,6-dione]) ylide, and 4-iodophenyliodonium-(5-[2,2- dimethyl-1,3-dioxane-4,6-dione]) ylide, two novel precursors for 4-[ 18F]fluoro-1-halobenzene, are reported.