An unexpected [1,5]-H shift in the synthesis of nitroanilines

Ian W. Davies; Jean François Marcoux; Jeremy D.O. Taylor; Peter G. Dormer; Robert J. Deeth; Félix Antoine Marcotte; David L. Hughes; Paul J. Reider

doi:10.1021/ol017149f

An unexpected [1,5]-H shift in the synthesis of nitroanilines

Ian W. Davies, Jean François Marcoux, Jeremy D.O. Taylor, Peter G. Dormer, Robert J. Deeth, Félix Antoine Marcotte, David L. Hughes, Paul J. Reider

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

14 Scopus citations

Abstract

Equation Presented Addition of methyl acetoacetate to 2-nitrovinamidinium hexafluorophosphate salts leads to the formation of anilines or phenols in good to excellent yields depending on the alkylamine substituents. Small substituents, e.g., pyrrolidine, lead to the formation of anilines while large substituents, e.g., N,N-diisopropyl, exclusively give phenols. Labeling studies implicate a [1,5]-H shift proceeding with excellent isotopic fidelity.

Original language	English (US)
Pages (from-to)	439-441
Number of pages	3
Journal	Organic letters
Volume	4
Issue number	3
DOIs	https://doi.org/10.1021/ol017149f
State	Published - Feb 7 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol017149f

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title = "An unexpected [1,5]-H shift in the synthesis of nitroanilines",

abstract = "Equation Presented Addition of methyl acetoacetate to 2-nitrovinamidinium hexafluorophosphate salts leads to the formation of anilines or phenols in good to excellent yields depending on the alkylamine substituents. Small substituents, e.g., pyrrolidine, lead to the formation of anilines while large substituents, e.g., N,N-diisopropyl, exclusively give phenols. Labeling studies implicate a [1,5]-H shift proceeding with excellent isotopic fidelity.",

author = "Davies, {Ian W.} and Marcoux, {Jean Fran{\c c}ois} and Taylor, {Jeremy D.O.} and Dormer, {Peter G.} and Deeth, {Robert J.} and Marcotte, {F{\'e}lix Antoine} and Hughes, {David L.} and Reider, {Paul J.}",

year = "2002",

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doi = "10.1021/ol017149f",

language = "English (US)",

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journal = "Organic letters",

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T1 - An unexpected [1,5]-H shift in the synthesis of nitroanilines

AU - Davies, Ian W.

AU - Marcoux, Jean François

AU - Taylor, Jeremy D.O.

AU - Dormer, Peter G.

AU - Deeth, Robert J.

AU - Marcotte, Félix Antoine

AU - Hughes, David L.

AU - Reider, Paul J.

PY - 2002/2/7

Y1 - 2002/2/7

N2 - Equation Presented Addition of methyl acetoacetate to 2-nitrovinamidinium hexafluorophosphate salts leads to the formation of anilines or phenols in good to excellent yields depending on the alkylamine substituents. Small substituents, e.g., pyrrolidine, lead to the formation of anilines while large substituents, e.g., N,N-diisopropyl, exclusively give phenols. Labeling studies implicate a [1,5]-H shift proceeding with excellent isotopic fidelity.

AB - Equation Presented Addition of methyl acetoacetate to 2-nitrovinamidinium hexafluorophosphate salts leads to the formation of anilines or phenols in good to excellent yields depending on the alkylamine substituents. Small substituents, e.g., pyrrolidine, lead to the formation of anilines while large substituents, e.g., N,N-diisopropyl, exclusively give phenols. Labeling studies implicate a [1,5]-H shift proceeding with excellent isotopic fidelity.

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EP - 441

JO - Organic letters

JF - Organic letters

IS - 3

ER -

An unexpected [1,5]-H shift in the synthesis of nitroanilines

Abstract

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