Tetrahedron

Amino acids; 13: Investigations on the synthesis of dl-serine from α-haloacrylic acid derivatives

F Effenberger, G Zoller

Index: Effenberger, Franz; Zoller, Gerhard Tetrahedron, 1988 , vol. 44, # 17 p. 5573 - 5582

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Citation Number: 8

Abstract

The alkoxide-catalyzed addition of alcohols 2 to α-chloroacrylonitrile (1) at-35° C gives rise to 3-alkoxy-2-chloropropanenitriles 3; at 0–5° C with excess 2 alkyl 3-alkoxy-2- chloropropanimidates 4 are obtained. The yields of 3 or 4 decrease with increasing pKa values of the alcohols 2. In the base-catalyzed addition of phenols 5 to 1, a temperature- dependent addition equilibrium is set up in which the position of equilibrium is shifted in ...

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