Recent advances in ether dealkylation

Weissman, Steven A.; Zewge, Daniel

doi:10.1016/j.tet.2005.05.041

Cited by 159 publications

(114 citation statements)

References 165 publications

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“…From a close analysis of the literature methods for ether dealkylation, [1,2,4] we did not find any general procedures for the cleavage of tert-butyl ethers.…”

Section: Introductionmentioning

confidence: 82%

“…1-tert-Butoxyoctane [4] (1a) 2-tert-butoxy-octane [4] (1b), (1S,2R,4R)-2-tert-butoxy-1-isopropyl-4-methylcyclohexane [4] (1c) 2-tert-butoxy-1,2-diphenylethanone [4] (1e), 1-tert-butoxynon-3-ene [4] (1f), (S)-ethyl 2-tert-butoxypropanoate [17] (1h), 1-tert-butoxybenzene [4] (1i), 1-tert-butoxynaphthalene [4] (1j), 2-tert-butoxynaphthalene [4] (1k), 1-tert-butoxy-4-methoxybenzene [18] (1m) 1-tert-butoxy-4-nitrobenzene [19] (1p), 1-tert-butoxy-4-fluorobenzene [4] (1q), 1-tert-butoxy-3-chlorobenzene [4] (1r) are completely characterized known compounds.…”

Section: Preparation Of the Starting Materials: Synthesis Of Tertbutymentioning

confidence: 99%

“…[2] Its scarce employment in organic synthesis is probably due to the harsh conditions required for its formation and its cleavage. [1,2] We recently developed a new method to obtain tertbutyl ethers via an unusual reaction of alcohols with Boc 2 O in the presence of MgClO 4 . [3] The protocol was very efficiently applied to a large variety of alkyl and aryl substrates.…”

Section: Introductionmentioning

confidence: 99%

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tert‐Butyl Ethers: Renaissance of an Alcohol Protecting Group. Facile Cleavage with Cerium(III) Chloride/Sodium Iodide

et al. 2006

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The tert-butoxy derivative is one of the most underused alcohol protecting groups. After having developed an easy and useful protocol for its introduction, we offer here a simple procedure for its removal by treatment with anhydrous CeCl 3 and NaI in CH 3 CN. The procedure led to the successful cleavage of aliphatic and aromatic tert-butyl ethers and was compatible with various other functionalities and protecting groups present in the molecule.

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“…From a close analysis of the literature methods for ether dealkylation, [1,2,4] we did not find any general procedures for the cleavage of tert-butyl ethers.…”

Section: Introductionmentioning

confidence: 82%

Section: Preparation Of the Starting Materials: Synthesis Of Tertbutymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

tert‐Butyl Ethers: Renaissance of an Alcohol Protecting Group. Facile Cleavage with Cerium(III) Chloride/Sodium Iodide

et al. 2006

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“…The removal of one of the methyl group of the DME ligand most likely arises from the reaction of Ar'SK with the coordinated DME on the Lewis acidic W center, similarly to the demethylation of methylethers by thiolate in the presence of Lewis acids [29].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Reactivity of a Pentacoordinated Thiolate-Based Imido-Alkylidene W(VI) Complexes

Allouche

Mougel

Grüning

et al. 2016

Oil Gas Sci. Technol. – Rev. IFP Energies nouvelles

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“…Among several reagents used for demethylating methyl aryl ethers 13 the most common ones are BBr 3 , AlCl 3 , pyridinium hydrochloride and hydrogen bromide dissolved in acetic acid. Pyridinium hydrochloride seems to be really attractive due to its low cost and ready availability.…”

Section: Introductionmentioning

confidence: 99%

A new method for the preparation of solvatochromic 5-(5-X-6-hydroxynaphthyl-2)-7H-indolo[1,2-a]quinolinium merocyanines

Sawicka

Soroka

Ga̧siorowska

2010

Polish Journal of Chemical Technology

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A new method for the preparation of 7H-indolo[1,2-a]quinolinium solvatochromic dye precursors has been investigated. 5-(6-Hydroxynaphthyl-2)-7,7-dimethyl-7H-indolo[1,2-a]quinolinium perchlorate, 5-(5-bromo-6-hydroxynaphthyl-2)-7,7-dimethyl-7H-indolo[1,2-a]quinolinium perchlorate and 5-(5-nitro-6-hydroxynaphthyl-2)-7,7-dimethyl-7H-indolo[1,2-a]quinolinium perchlorate were obtained via demethylation of the corresponding 5-(5-X-6-methoxynaphthyl-2)-7,7-dimethyl-7H-indolo[1,2-a]quinolinium salts. The application of pyridinium hydrochloride in the demethylation of the methoxy perchlorates allowed to obtain the products with the almost quantitative yield in a very short time, especially when the reaction was carried out using microwave irradiation.

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Recent advances in ether dealkylation

Cited by 159 publications

References 165 publications

tert‐Butyl Ethers: Renaissance of an Alcohol Protecting Group. Facile Cleavage with Cerium(III) Chloride/Sodium Iodide

tert‐Butyl Ethers: Renaissance of an Alcohol Protecting Group. Facile Cleavage with Cerium(III) Chloride/Sodium Iodide

Synthesis and Reactivity of a Pentacoordinated Thiolate-Based Imido-Alkylidene W(VI) Complexes

A new method for the preparation of solvatochromic 5-(5-X-6-hydroxynaphthyl-2)-7H-indolo[1,2-a]quinolinium merocyanines

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