NOVEL METHOD FOR SELECTIVE DEPROTECTION OF POLY ARYL METHYL ETHERS BY ANTIMONY (V) CHLORIDE

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SAADATI FARIBA; MEFTAH BOUSHEHRI HAMID

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Seminar Paper

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Seminar: IRANIAN SEMINAR OF ORGANIC CHEMISTRY
Year:2012 | Issue:19

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Title

NOVEL METHOD FOR SELECTIVE DEPROTECTION OF POLY ARYL METHYL ETHERS BY ANTIMONY (V) CHLORIDE

Author(s)

SAADATI FARIBA | MEFTAH BOUSHEHRI HAMID

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Abstract

THE O-DEALKYLATION OF ETHERS, OR ETHER CLEAVAGE, REMAINS AN INTEGRAL FUNCTIONAL GROUP DEPROTECTION STEP TO UNMASK A HYDROXYL GROUP. THE REAGENT SELECTIVITY RELATIVE TO OTHER TYPES OF HYDROXYL PROTECTING GROUPS WILL BE HIGHLIGHTED, AS THIS REMAINS A KEY FACTOR IN THE CHOICE OF REAGENT, ESPECIALLY IN POLY FUNCTIONAL MOLECULES [1]. METHYL ETHERS OF BOTH ALIPHATIC AND AROMATIC MOIETIES ARE ONE OF THEM, BUT A MAJOR DRAWBACK INVOLVED IN THIS IS THEIR ROBUSTNESS AND THE DIFFICULTIES ENCOUNTERED DURING THEIR CLEAVAGE [2]. AROMATIC METHYL ETHERS ARE MORE EASILY CLEAVED THAN THEIR ALIPHATIC COUNTERPARTS [3]. THE CHOICE OF REAGENT CAPABLE OF CLEAVING THE ALKYL ARYL ETHER BOUND IS VERY IMPORTANT.WE HAVE FOUND THAT THE DEMETHYLATION OF ARYL METHYL ETHERS CAN BE SELECTIVITY ACHIEVED BY THE TREATMENT OF ANTIMONY PENTACHLORIDE IN ACETONITRILE IN EXCELLENT YIELDS.THE ABOVE STUDIES PROMPTED US TO SELECT THE USE OF SBCL5 IN CH3CN ANHYDROUS UNDER ROOM TEMPERATURE TO PROBE THE SCOPE OF THE DEMETHYLATION REACTION. SBCL5 AS LEWIS ACID CAN PLAY CERTAINLY DIFFERENT ROLE ON POLY-SUBSTITUTED ETHERS COMPOUNDS. IN THIS CASE, SBCL5 SELECTIVELY DEPROTECT ONE OF THE SEVERAL METHOXY GROUPS ON SUBSTRATE. UNDER THE RELATIVELY MILD REACTION CONDITIONS, THE METHYL GROUP CAN BE READILY CLEAVED TO AFFORD CLEAN PHENOL-DERIVED PRODUCT EXCELLENT YIELDS. THE VERSATILE BY-PRODUCTS CAN BE CONVENIENTLY REMOVED BYCOLUMN CHROMATOGRAPHY.

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APA: Copy

SAADATI, FARIBA, & MEFTAH BOUSHEHRI, HAMID. (2012). NOVEL METHOD FOR SELECTIVE DEPROTECTION OF POLY ARYL METHYL ETHERS BY ANTIMONY (V) CHLORIDE. IRANIAN SEMINAR OF ORGANIC CHEMISTRY. SID. https://sid.ir/paper/909512/en

Vancouver: Copy

SAADATI FARIBA, MEFTAH BOUSHEHRI HAMID. NOVEL METHOD FOR SELECTIVE DEPROTECTION OF POLY ARYL METHYL ETHERS BY ANTIMONY (V) CHLORIDE. 2012. Available from: https://sid.ir/paper/909512/en

IEEE: Copy

FARIBA SAADATI, and HAMID MEFTAH BOUSHEHRI, “NOVEL METHOD FOR SELECTIVE DEPROTECTION OF POLY ARYL METHYL ETHERS BY ANTIMONY (V) CHLORIDE,” presented at the IRANIAN SEMINAR OF ORGANIC CHEMISTRY. 2012, [Online]. Available: https://sid.ir/paper/909512/en

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