A new conversion of primary nitro compounds into nitriles

Laurent El Kaim; Ariane Gacon

doi:10.1016/S0040-4039(97)00627-8

A new conversion of primary nitro compounds into nitriles

Laurent El Kaim
, Ariane Gacon

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	3391-3394
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4039(97)00627-8
Publication status	Published - 12 May 1997

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title = "A new conversion of primary nitro compounds into nitriles",

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.",

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T1 - A new conversion of primary nitro compounds into nitriles

AU - El Kaim, Laurent

AU - Gacon, Ariane

PY - 1997/5/12

Y1 - 1997/5/12

N2 - 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.

AB - 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.

U2 - 10.1016/S0040-4039(97)00627-8

DO - 10.1016/S0040-4039(97)00627-8

M3 - Article

AN - SCOPUS:0030976229

SN - 0040-4039

VL - 38

SP - 3391

EP - 3394

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

A new conversion of primary nitro compounds into nitriles

Abstract

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