Volume 22, Issue 39
Preparative Organic Chemistry
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ChemInform Abstract: Selective Reduction of Disulfides by Tris(2-carboxyethyl)phosphine.

J. A. BURNS

J. A. BURNS

Dep. Chem., Harvard Univ., Cambridge, MA 02138, USA

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J. C. BUTLER

J. C. BUTLER

Dep. Chem., Harvard Univ., Cambridge, MA 02138, USA

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J. MORAN

J. MORAN

Dep. Chem., Harvard Univ., Cambridge, MA 02138, USA

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G. M. WHITESIDES

G. M. WHITESIDES

Dep. Chem., Harvard Univ., Cambridge, MA 02138, USA

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First published: October 1, 1991

Abstract

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ChemInform Abstract

Tris(2-cyanoethyl)phosphine (I) is hydrolyzed in hydrochloric acid to give tris(2-carboxyethyl)phosphine hydrochloride (II). This compound reduces preferentially more strained disulfides rapidly and quantitatively in water at pH 4.5. (Mechanism).

chemical structure image

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