35024-12-5

Basic information

• Product Name: Iodonium, phenyl-, 4,4-dimethyl-2,6-dioxocyclohexylide
• CAS NO: 35024-12-5
• Molecular Formula: C14H15IO2
• Molecular Weight: 342.176
• Mol File: 35024-12-5.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: Iodonium, phenyl-, 4,4-dimethyl-2,6-dioxocyclohexylide(CAS DataBase Reference)
• NIST Chemistry Reference: Iodonium, phenyl-, 4,4-dimethyl-2,6-dioxocyclohexylide(35024-12-5)
• EPA Substance Registry System: Iodonium, phenyl-, 4,4-dimethyl-2,6-dioxocyclohexylide(35024-12-5)

Safety Data

• Hazardous Substances Data: 35024-12-5(Hazardous Substances Data)

Upstream product

• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 591-50-4 iodobenzene 
• 126-81-8 dimedone 
• 26735-53-5 iodobenzene difluoride 
• 536-80-1 iodosylbenzene 
• 121434-38-6 phenyliodonium bis(phenylsulfonyl)-methylide 
• 1807-68-7 diazodimedone 

Downstream Products

• 94569-94-5 2-iodo-5,5-dimethyl-3-phenoxycyclohex-2-en-1-one 
• 56995-07-4 4',4',6,6-tetramethyl-6,7-dihydro-2'H,6'H-spiro[1,3-benzoxathiol-2,1'-cyclohexan]-2',4,6'(5H)-trion 
• 95617-26-8 6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1,3-benzoxathiole-2-thione 
• 95617-27-9 2-(6,6-Dimethyl-4-oxo-4,5,6,7-tetrahydro-benzo[1,3]oxathiol-2-ylidene)-5,5-dimethyl-cyclohexane-1,3-dione 
• 113760-31-9 C₁₈H₂₀O₄S₄ 
• 18150-87-3 6,6-dimethyl-4-oxo-2-phenyl-4,5,6,7-tetrahydrobenzofuran 
• 7298-89-7 2-chloro-5,5-dimethyl-1,3-cyclohexanedione 
• 114004-77-2 (2-Benzoyloxy-4,4-dimethyl-6-oxo-cyclohex-1-enyl)-phenyl-iodonium; chloride 
• 6267-39-6 3-ethoxy-5,5-dimethyl-2-cyclohexen-1-one 
• 18369-68-1 3-acetoxy-2-bromo-5,5-dimethylcyclohex-2-enone 
• 72035-56-4 5,5-dimethyl-3-phenoxycyclohex-2-en-1-one 

Relevant articles and documents

CO2-activated NaClO-5H2O enabled smooth oxygen transfer to iodoarene: A highly practical synthesis of iodosylarene

A safe, rapid, and environmentally friendly synthesis of iodosylarene (ArIO) has been developed using NaClO under a carbon dioxide (CO2) atmosphere. Exposure of iodoarene to NaClO-5H2O in acetonitrile under CO2 (1 atm) resulted in the clean formation of ArIO within 10 minutes in high yield. The absence of a base in this method enables the direct use of in-situ-generated iodosylarene not only for a variety of oxidative transformations (synthesis of sulfilimine, pentavalent bismuth, benzyne adduct, etc.), but also for the synthesis of iodonium ylide and imino-λ3-iodane in one pot.

Rh(iii)-Catalyzed C(sp2)-H functionalization/cyclization cascade of: N -carboxamide indole and iodonium reagents for access to indoloquinazolinone derivatives

A rhodium-catalyzed synthesis of indoloquinazolinone from a readily available hypervalent iodonium reagent and N-carboxamide indole was developed. The protocol features broad functional group tolerance, mild conditions, and excellent yields. The target products were obtained simply by filtration, without tedious column chromatography. Notably, the noble metal catalyst system can be recycled effectively at least ten times. The strategy may be amenable to industrial production.

Harnessing hypervalent iodonium ylides as carbene precursors: C-H activation of: N -methoxybenzamides with a Rh(iii)-catalyst

Hypervalent iodonium ylides expeditiously generate carbenes which undergo domino intermolecular C-H activation followed by intramolecular condensation in the presence of N-methoxybenzamide as a starting material and a Rh(iii)-catalyst to afford dihydrophenanthridines. KIE studies and DFT calculations were performed to substantiate the mechanistic pathway. To extend the synthetic utilisation, fluorescent pyranoisocoumarins were achieved by using Rh(iii)-catalyzed peri-C-H/O-H activation/annulation reactions.