Tetrahedron letters

A new conversion of primary nitro compounds into nitriles

L El Kaim, A Gacon

Index: El Kaim, Laurent; Gacon, Ariane Tetrahedron Letters, 1997 , vol. 38, # 19 p. 3391 - 3394

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Citation Number: 21

Abstract

The reaction of primary nitro compounds with isocyanides and isocyanates in the presence of a base leads to a new preparation of nitriles. The reaction probably proceeds through the in situ formation of a nitrile oxide followed by a fast oxygen transfer with the isocyanide. Combined with the Knovenagel addition of nitromethane to cyclic ketone, this reaction brings a highly effective regioselective formation of cyclic α-β unsaturated nitriles.