Tetrahedron letters

Deuteration of α, β-acetylenic esters, amides, or carboxylic acids without using deuterium gas: synthesis of 2, 2, 3, 3-tetradeuterioesters, amides, or acids

JM Concellón, H Rodrı́guez-Solla, C Concellón

Index: Concellon, Jose M.; Rodriguez-Solla, Humberto; Concellon, Carmen Tetrahedron Letters, 2004 , vol. 45, # 10 p. 2129 - 2131

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Citation Number: 10

Abstract

An easy, simple, rapid, and nonhazardous deuteration of the C–C triple bond of α, β- acetylenic esters, amides, or acids by means of samarium diiodide in the presence of D2O, provides an efficient method for synthesizing 2, 2, 3, 3-tetradeuterioesters, amides, or carboxylic acids, respectively. When H2O is used instead of D2O, saturated carboxylic esters, amides, or acids were isolated. A mechanism to explain these reduction reactions ...