Phenyliodonium 4,4‐Dimethyl‐2,6‐dioxocyclohexylide

[35024-12-5],[81447-29-2] C14H15IO2 (MW 342.18) InChI = 1S/C14H15IO2/c1-14(2)8-11(16)13(12(17)9-14)15-10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3 InChIKey = IERLOSGMYPXIOS-UHFFFAOYSA-N (reagent used for 1,3-dipolar cycloaddition, CH insertion, cyclopropanation, oxidative carbonylation, aryl fluorination, and thermal rearrangement reactions) Physical Data: mp 129–130 °C, decomposes upon heating. Solubility: insoluble in H2O, soluble in DMSO, chlorinated organic solvents such as dichloromethane, and insoluble in most other organic solvents, including ether, acetone, benzene, and ethyl acetate. Reagent will decompose in protic organic solvents. Form Supplied in: white or slightly yellow granules. Purification: the crude solid is triturated with hexanes followed by simple filtration. Handling, Storage, and Precautions: avoid exposure to moist air, water, and temperatures above 130 °C. The ylide is stable at −30 °C for a prolonged period of time. The ylide isomerizes into the corresponding iodo-ether upon heating in various solvents. Store under inert atmosphere, refrigerated, in a tightly closed container. No information is available on the carcinogenicity, teratogenicity, mutagenicity, and neurotoxicity. Phenyliodonium 4,4-dimethyl-2,6-dioxocyclohexylide is not listed by the International Agency for Research on Cancer (IARC). Preparation: prepared in 90% yield by reacting a solution of 5,5-dimethyl-1,3-cyclohexanedione and iodobenzene diacetate in dichloromethane at room temperature for 2–3 h. Subsequently, the dichloromethane solution is washed with aqueous 5% KOH and brine. The combined organic layers are dried with magnesium sulfate, filtered, and evaporated to dryness. This method provides a general route for the synthesis of iodonium ylides from 1,3-dicarbonyl compounds.

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