86396-03-4

Basic information

• Product Name: Iodonium, phenyl-, 4-methyl-2,6-dioxocyclohexylide
• CAS NO: 86396-03-4
• Molecular Formula: C13H13IO2
• Molecular Weight: 328.15
• Mol File: 86396-03-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Iodonium, phenyl-, 4-methyl-2,6-dioxocyclohexylide(CAS DataBase Reference)
• NIST Chemistry Reference: Iodonium, phenyl-, 4-methyl-2,6-dioxocyclohexylide(86396-03-4)
• EPA Substance Registry System: Iodonium, phenyl-, 4-methyl-2,6-dioxocyclohexylide(86396-03-4)

Safety Data

• Hazardous Substances Data: 86396-03-4(Hazardous Substances Data)

Upstream product

• 4341-24-6 5-methylcyclohexan-1,3-dione 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 536-80-1 iodosylbenzene 

Downstream Products

• 86396-17-0 5-Methyl-cyclohexane-1,2,3-trione 
• 1160219-56-6 6-methyl-2-(phenylimino)-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-one 
• 1391041-90-9 2-(4-chlorophenylimino)-6-methyl-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-one 
• 1391041-96-5 6-methyl-2-(2,4,6-trichlorophenylimino)-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)one 
• 92898-22-1 6-methyl-2-phenyl-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one 
• 1415261-38-9 C₂₁H₁₈O₃ 
• 1415261-33-4 3,3-diphenyl-6-methyl-6,7-dihydro-benzofuran-2,4(3H,5H)-dione 
• 1415261-47-0 2-chloro-5-methyl-3-oxocyclohex-1-enyl 2,2-diphenylethanoate 

Relevant articles and documents

Rh(III)-Catalyzed Chemodivergent Annulations between Indoles and Iodonium Carbenes: A Rapid Access to Tricyclic and Tetracyclic N-Heterocylces

Herein, we report an acid-controlled highly tunable selectivity of Rh(III)-catalyzed [4 + 2] and [3 + 3] annulations of N-carboxamide indoles with iodonium ylides lead to form synthetically important tricyclic and tetracyclic N-heterocycles. Here, iodonium ylide serves as a carbene precursor. The protocol proceeds under operationally simple conditions and provides novel tricyclic and tetracyclic scaffolds such as 3,4-dihydroindolo[1,2-c]quinazoline-1,6(2H,5H)-dione and 1H-[1,3]oxazino[3,4-a]indol-1-one derivatives with a broad range of functional group tolerance and moderate to excellent yields. Furthermore, the protocol synthetic utility was extended for various chemical transformations and was easily scaled up to a large-scale level.

Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C-H Activation

The rhodium(III)-catalyzed coupling of C-H substrates with iodonium ylides has been realized for the efficient synthesis of diverse cyclic skeletons, where the iodonium ylides have been identified as efficient and outstanding carbene precursors. The reaction systems are applicable to both sp2 and sp3 C-H substrates under mild and redox-neutral conditions. The catalyst loading can be as low as 0.5 mol % in a gram-scale reaction. Representative products exhibit cytotoxicity toward human cancer cells at nanomolar levels.

Fused dihydrofurans from the one-pot, three-component reaction of 1,3-cyclohexanedione, iodobenzene diacetate and alkenes

The one-pot, three-component reactions of substituted 1,3- cyclohexanediones, iodobenzene diacetate and alkenes, under photochemical activation, yields fused dihydrofuran derivatives in good yield via the in situ formation of iodonium ylides.