Tetrahedron letters

Synthesis of 2-(2′-hydroxyphenyl) pyridine-N-oxide and its thermal decomposition as a model reaction of orellanine deoxidation

WZ Antkowiak, WP Gessner

Index: Antkowiak, Wieslaw Z.; Gessner, Wieslaw P. Tetrahedron Letters, 1984 , vol. 25, # 36 p. 4045 - 4048

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Citation Number: 20

Abstract

Abstract 2-Methoxyphenylmagnesium bromide was reacted with 2-nitropyridine-N-oxide and demethylated to give 2-(2′-hydroxyphenyl) pyridine-N-oxide (II) which was found to undergo a thermal deoxidation to the free base (VI); the process is interpreted as a [1.5] oxygen shift followed by decomposition of the hydroperoxide intermediate.