Folding-promoted TBAX-mediated selective demethylation of methoxybenzene-based macrocyclic aromatic pentamers

Zhiyun Du; Bo Qin; Chang Sun; Ying Liu; Xi Zheng; Kun Zhang; Allan H. Conney; Huaqiang Zeng

doi:10.1039/c2ob25160d

Folding-promoted TBAX-mediated selective demethylation of methoxybenzene-based macrocyclic aromatic pentamers

Zhiyun Du, Bo Qin, Chang Sun, Ying Liu, Xi Zheng, Kun Zhang, Allan H. Conney, Huaqiang Zeng

Ernest Mario School of Pharmacy, Chemical Biology

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

Described in this study is the ability of tetrabutylammonium salts (TBAX) to mediate an efficient mono- or di-demethylation removing one or two out of five aromatic methoxy methyl groups situated in similar chemical microenvironments in a H-bonded macrocyclic aromatic pentamer. These demethylations are found to be both chemo- and regioselective, and promoted by the H-bonding directed folding of the macrocyclic backbone.

Original language	English (US)
Pages (from-to)	4164-4171
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	21
DOIs	https://doi.org/10.1039/c2ob25160d
State	Published - Jun 7 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Described in this study is the ability of tetrabutylammonium salts (TBAX) to mediate an efficient mono- or di-demethylation removing one or two out of five aromatic methoxy methyl groups situated in similar chemical microenvironments in a H-bonded macrocyclic aromatic pentamer. These demethylations are found to be both chemo- and regioselective, and promoted by the H-bonding directed folding of the macrocyclic backbone.",

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AU - Du, Zhiyun

AU - Qin, Bo

AU - Sun, Chang

AU - Liu, Ying

AU - Zheng, Xi

AU - Zhang, Kun

AU - Conney, Allan H.

AU - Zeng, Huaqiang

PY - 2012/6/7

Y1 - 2012/6/7

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AB - Described in this study is the ability of tetrabutylammonium salts (TBAX) to mediate an efficient mono- or di-demethylation removing one or two out of five aromatic methoxy methyl groups situated in similar chemical microenvironments in a H-bonded macrocyclic aromatic pentamer. These demethylations are found to be both chemo- and regioselective, and promoted by the H-bonding directed folding of the macrocyclic backbone.

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ER -

Folding-promoted TBAX-mediated selective demethylation of methoxybenzene-based macrocyclic aromatic pentamers

Abstract

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