Synthesis of Tetrafluorocatechol

Ramanathan, S.; Sang, Dayong; Kumar, Vivek; Lemal, David M.

doi:10.1002/9781118409466.ch41

Cited by 2 publications

(2 citation statements)

References 13 publications

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“…Unexpectedly, 1,4benzodioxane (6y) remained intact under these conditions, although it was known that 2-ethyl-5,6,7,8-tetrafluorobenzo-1,4-dioxane could be cleaved successfully by AlI 3 . 40 Some of these substrates had been deprotected by our group using the AlI 3 -CaO system. 28 A comparison showed that 6a, 6a′, 6j, 6k, 6k′, 6l, 6m, 6q, and 6r were deprotected as efficiently by the two methods.…”

Section: Paper Syn Thesismentioning

confidence: 99%

Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide–Dimethyl Sulfoxide

Sang

Tian²,

Tu³

et al. 2018

Synthesis

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Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o-hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.

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Section: Paper Syn Thesismentioning

confidence: 99%

Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide–Dimethyl Sulfoxide

Sang

Tian²,

Tu³

et al. 2018

Synthesis

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“…60 A markedly improved method consisted of treating dioxin 79b with AlI 3 to furnish the catechol in 79% yield (Scheme 5E). 61 (VI) The regioselective preference of AlI 3 for cleaving alkyl aryl ethers has been applied in evaluation of nonylphenol ethoxylates (NPEO n ) and octylphenol ethoxylates (OPEO n ) in textiles and leathers (Scheme 5F). These ethoxylates are non-ionic surfactants prohibited for domestic use.…”

Section: Partial Demethylationmentioning

confidence: 99%

Application of aluminum triiodide in organic synthesis

Tian¹,

Sang²

2015

Arkivoc

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The multifaceted reactivity of aluminum triiodide (AlI 3 ) is reviewed. The oxophilic character of the Lewis acid enables the formation of coordination complexes with esters, ethers, oxiranes, diols, Noxides, and sulfoxides that decompose spontaneously to afford acids, alcohols and olefins via ester and ether cleavage, deoxygenation of oxiranes, and deoxydehydration of diols, respectively. As an iodide ion source and hydrogen iodide precursor, the reagent allows iodination and reduction of Noxides, sulfoxides and azides as well as hydroiodination of alkenes and alkynes. Aluminum enolates, generated by treatment of -haloketones with AlI 3 , provide accesses to -hydroxy ketones, 1,5-diones, and β-iodo Morita-Baylis-Hillman esters.

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Synthesis of Tetrafluorocatechol

Cited by 2 publications

References 13 publications

Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide–Dimethyl Sulfoxide

Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide–Dimethyl Sulfoxide

Application of aluminum triiodide in organic synthesis

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