Hard acid and soft nucleophile system. 2. Demethylation of methyl ethers of alcohol and phenol with an aluminum halide-thiol system

Node, Manabu; Nishide, Kiyoharu; Fuji, Kaoru; Fujita, Eiichi

doi:10.1021/jo01310a003

Cited by 160 publications

(83 citation statements)

References 6 publications

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“…[39] Methylene acetals are usually obtained by reaction with a methylene dihalide. [40,41] The resulting methylenedioxy group is relatively stable, but can be efficiently deprotected by use of a suitable Lewis acid such as a boron [42,43] or aluminium [44,45] halide. Acetone can be used to convert catechols into the corresponding acetonides [46] which are hydrolyzed in acidic conditions.…”

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confidence: 99%

Redox‐Active Catechol‐Functionalized Molecular Rods: Suitable Protection Groups and Single‐Molecule Transport Investigations

Weibel

Błaszczyk²,

Hänisch³

et al. 2007

Eur J Org Chem

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The synthesis of molecular rod 1 comprising a central redox‐active unit and two terminal acetyl‐protected sulfur groups is reported. Various protecting groups for the catechol moiety were investigated and protected precursors 14–18 were synthesized. In particular, ethyl orthoformate 17 can be easily and selectively deprotected in mild acidic conditions ruling out the need for a strong Lewis acid like boron tribromide. The redox activity of 1 was confirmed by cyclic voltammetric investigations. Gold–molecule–gold junctions were formed with the dimethyl‐protected rod 18. Single‐molecule transport investigations using this molecular rod revealed a set of three single‐junction conductance values varying over two orders of magnitude.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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confidence: 99%

Redox‐Active Catechol‐Functionalized Molecular Rods: Suitable Protection Groups and Single‐Molecule Transport Investigations

Weibel

Błaszczyk²,

Hänisch³

et al. 2007

Eur J Org Chem

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“…The use of AlCl 3 /EtSH reagent [10] for demethylation of aromatic ethers has been reported. However, treatment of osthol with AlCl 3 /EtSH at room temperature resulted in direct cyclisation by transetherification reaction yielding pyrano coumarin, 3.…”

Section: Resultsmentioning

confidence: 99%

A New Synthetic Route to Dihydrobenzopyran Via Tandem Demethylation Cyclisation

Gopalakrishnan¹,

Kasinath²,

Singh³

et al. 2000

Molecules

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“…Two approaches were attempted: treatment of 7 with either Lawesson reagent [11,12] or P 4 S 10 (note that 6 was obtained from 5 using P 4 S 10 ) [13,14] and demethylation of 6 with HBr (only 7 was obtained) or with C 2 H 5 SH/ AlCl 3 [15,16] (no reaction was observed).…”

Section: Resultsmentioning

confidence: 99%

Reaction of 4-Hydroxyacridin-9(10H)-one and 4-Hydroxyacridine-9(10H)-thione with α,ω-Alkyl Dibromides

Galy

Vichet

et al. 1998

Monatshefte fuer Chemie

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Starting from 4-hydroxyacridin-9(10H )-one (1) and 4-hydroxyacridine-9(10H)-thione (2), a series of bis-derivatives was prepared, among them the bridged bis-acridin-(10H )-ones 9±14 and the bis-mercapto-(9H)-acridines 15±18. The reactivity of the 2-and 4-hydroxy series was compared; it was found that it is harder to demethylate 4-methoxy derivatives than their 2-methoxy analogues.Reaktion von 4-Hydroxyacridin-9(10H)-on und 4-Hydroxyacridin-9(10H)-thion mit ,x-Alkyldibromiden Zusammenfassung. Ausgehend von 4-Hydroxyacridin-9(10H)-on (1) und 4-Hydroxyacridin-9(10H)-thion (2) wurde eine Serie von bis-Derivaten, unter ihnen die verbru Èckten bis-Acridin-9(10H)-one 9±14 und die bis-Mercapto-(9H)-acridine 15±18, hergestellt. Die Reaktivita Èt der 2-und 4-Hydroxyderivate wurde verglichen; es wurde festgestellt, daû die 4-Methoxyderivate schwerer zu demethylieren sind als die 2-Methoxyderivate.

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Hard acid and soft nucleophile system. 2. Demethylation of methyl ethers of alcohol and phenol with an aluminum halide-thiol system

Cited by 160 publications

References 6 publications

Redox‐Active Catechol‐Functionalized Molecular Rods: Suitable Protection Groups and Single‐Molecule Transport Investigations

Redox‐Active Catechol‐Functionalized Molecular Rods: Suitable Protection Groups and Single‐Molecule Transport Investigations

A New Synthetic Route to Dihydrobenzopyran Via Tandem Demethylation Cyclisation

Reaction of 4-Hydroxyacridin-9(10H)-one and 4-Hydroxyacridine-9(10H)-thione with α,ω-Alkyl Dibromides

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