Synthesis and electrochemical reduction of 2-methyl-4-((9-oxo-9H-thioxanthen-2-yl)methoxy)benzoate and its S,S-dioxide in dimethylformamide
L. A. SHUNDRIN, I. A. OS’KINA, I. G. IRTEGOVA
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia
Keywords: thioxanthone, electrochemical reduction, radical anion, cyclic voltammetry, electron paramagnetic resonance spectroscopy
Abstract
The reaction of 2-(bromomethyl)-9H-thioxanthen-9-one with p-hydroxymethyl benzoate leads to 2-methyl-4-((9-oxo-9H-thioxanthen-2-yl)methoxy)benzoate 1, which is converted into the corresponding S,S-dioxide 2 upon oxidation with hydrogen peroxide. The first stages of electrochemical reduction of compounds 1, 2 in dimethylformamide are reversible one-electron processes with the formation of long-lived radical anions [1].-, [2].-. The second stage of electrochemical reduction of compound 2 is a one-electron irreversible process.
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