Differential cleavage of arylmethyl ethers: Reactivity of 2,6-dimethoxybenzyl ethers

J. R. Falck; D. K. Barma; Rachid Baati; Charles Mioskowski

doi:10.1002/1521-3773(20010401)40:7<1281::AID-ANIE1281>3.0.CO;2-B

Differential cleavage of arylmethyl ethers: Reactivity of 2,6-dimethoxybenzyl ethers

J. R. Falck, D. K. Barma, Rachid Baati, Charles Mioskowski

Biochemistry

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

36 Scopus citations

Abstract

CrCl₂/LiI selectively cleave benzyl ethers and methoxy-substituted benzyl ethers (see scheme) in the order: C₆H₅CH₂OR < 4-MeOC₆H₄CH₂OR < 3,4-(MEO)₂C₆H₃CH₂OR < 2,6-(MeO)₂C₆H₃CH₂OR. In contrast, C₆H₅CH₂OR is more readily cleaved than 2,6-(MeO)₂C₆H₃CH₂OR during catalytic hydrogenolysis while 3,4-(MeO)₂C₆H₃CH₂OR is cleaved faster than 2,6-(MeO)₂C₆H₃CH₂OR with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).

Original language	English (US)
Pages (from-to)	1281-1283
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	40
Issue number	7
DOIs	https://doi.org/10.1002/1521-3773(20010401)40:7<1281::AID-ANIE1281>3.0.CO;2-B
State	Published - Apr 2 2001

Keywords

Chemoselectivity
Chromium
Cleavage reactions
Protecting groups
Reductions

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/1521-3773(20010401)40:7<1281::AID-ANIE1281>3.0.CO;2-B

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title = "Differential cleavage of arylmethyl ethers: Reactivity of 2,6-dimethoxybenzyl ethers",

abstract = "CrCl2/LiI selectively cleave benzyl ethers and methoxy-substituted benzyl ethers (see scheme) in the order: C6H5CH2OR < 4-MeOC6H4CH2OR < 3,4-(MEO)2C6H3CH2OR < 2,6-(MeO)2C6H3CH2OR. In contrast, C6H5CH2OR is more readily cleaved than 2,6-(MeO)2C6H3CH2OR during catalytic hydrogenolysis while 3,4-(MeO)2C6H3CH2OR is cleaved faster than 2,6-(MeO)2C6H3CH2OR with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).",

keywords = "Chemoselectivity, Chromium, Cleavage reactions, Protecting groups, Reductions",

author = "Falck, {J. R.} and Barma, {D. K.} and Rachid Baati and Charles Mioskowski",

year = "2001",

month = apr,

day = "2",

doi = "10.1002/1521-3773(20010401)40:7<1281::AID-ANIE1281>3.0.CO;2-B",

language = "English (US)",

volume = "40",

pages = "1281--1283",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

number = "7",

}

TY - JOUR

T1 - Differential cleavage of arylmethyl ethers

T2 - Reactivity of 2,6-dimethoxybenzyl ethers

AU - Falck, J. R.

AU - Barma, D. K.

AU - Baati, Rachid

AU - Mioskowski, Charles

PY - 2001/4/2

Y1 - 2001/4/2

N2 - CrCl2/LiI selectively cleave benzyl ethers and methoxy-substituted benzyl ethers (see scheme) in the order: C6H5CH2OR < 4-MeOC6H4CH2OR < 3,4-(MEO)2C6H3CH2OR < 2,6-(MeO)2C6H3CH2OR. In contrast, C6H5CH2OR is more readily cleaved than 2,6-(MeO)2C6H3CH2OR during catalytic hydrogenolysis while 3,4-(MeO)2C6H3CH2OR is cleaved faster than 2,6-(MeO)2C6H3CH2OR with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).

AB - CrCl2/LiI selectively cleave benzyl ethers and methoxy-substituted benzyl ethers (see scheme) in the order: C6H5CH2OR < 4-MeOC6H4CH2OR < 3,4-(MEO)2C6H3CH2OR < 2,6-(MeO)2C6H3CH2OR. In contrast, C6H5CH2OR is more readily cleaved than 2,6-(MeO)2C6H3CH2OR during catalytic hydrogenolysis while 3,4-(MeO)2C6H3CH2OR is cleaved faster than 2,6-(MeO)2C6H3CH2OR with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).

KW - Chemoselectivity

KW - Chromium

KW - Cleavage reactions

KW - Protecting groups

KW - Reductions

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DO - 10.1002/1521-3773(20010401)40:7<1281::AID-ANIE1281>3.0.CO;2-B

M3 - Article

AN - SCOPUS:0035794912

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EP - 1283

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 7

ER -

Differential cleavage of arylmethyl ethers: Reactivity of 2,6-dimethoxybenzyl ethers

Abstract

Keywords

ASJC Scopus subject areas

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