Preparation of 2-picolylarsonic acid and its reductive cleavage by ascorbic acid/iodine and by thiophenol

PV Ioannou, PA Afroudakis…

Index: Ioannou, Panayiotis V. Phosphorus, Sulfur and Silicon and Related Elements, 2002 , vol. 177, # 1 p. 1 - 14

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Citation Number: 3

Abstract

Contrary to dialkylaminoethyl halides, 2-picolyl chloride reacts with alkaline arsenite to give nearly quantitative yields 2-picolylarsonic acid. This acid is decomposed by ascorbic acid in the presence of catalytic amounts of iodine to 2-picoline and arsenious acid, most likely by hydride transfer from the ascorbic acid. Thiophenol decomposes this arsonic acid very quickly to 2-picoline, diphenyl disulfide and triphenyl trithioarsenite. In this case a proton ...