Volume 18, Issue 24
Preparative Organic Chemistry
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ChemInform Abstract: Calcium in Liquid Ammonia for the Reduction of Benzyl Ethers. Mechanistic Clues Derived from Chemoselectivity Studies.

J. R. HWU

J. R. HWU

Dep. Chem., Johns Hopkins Univ., Baltimore, MD 21218, USA

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V. CHUA

V. CHUA

Dep. Chem., Johns Hopkins Univ., Baltimore, MD 21218, USA

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J. E. SCHROEDER

J. E. SCHROEDER

Dep. Chem., Johns Hopkins Univ., Baltimore, MD 21218, USA

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R. E. JUN. BARRANS

R. E. JUN. BARRANS

Dep. Chem., Johns Hopkins Univ., Baltimore, MD 21218, USA

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K. P. KHOUDARY

K. P. KHOUDARY

Dep. Chem., Johns Hopkins Univ., Baltimore, MD 21218, USA

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N. WANG

N. WANG

Dep. Chem., Johns Hopkins Univ., Baltimore, MD 21218, USA

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J. M. WETZEL

J. M. WETZEL

Dep. Chem., Johns Hopkins Univ., Baltimore, MD 21218, USA

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First published: June 16, 1987

Abstract

The benzylic ethers (I) are cleaved by calcium in liquid ammonia to give the corresponding alcohols (II).

ChemInform Abstract

The benzylic ethers (I) are cleaved by calcium in liquid ammonia to give the corresponding alcohols (II). This reagent is more selective than lithium in liquid ammonia as is proved by the reduction of (III) which yields different ratios of (IV) and (V). (Mechanism).

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