Mild and selective sodium azide mediated cleavage of p-nitrobenzoic esters

José A. Gómez-Vidal; Michael T. Forrester; Richard B. Silverman

doi:10.1021/ol016104b

Mild and selective sodium azide mediated cleavage of p-nitrobenzoic esters

José A. Gómez-Vidal, Michael T. Forrester, Richard B. Silverman^*

^*Corresponding author for this work

Chemistry

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

39 Scopus citations

Abstract

matrix presented A mild and selective cleavage of p-nitrobenzoic esters by sodium azide in methanol is reported. This new methodology is mild enough for use with acid-or base-sensitive compounds. No elimination byproducts are formed. Fmoc-and trifluoroacetyl-amino protecting groups, benzyl esters, and ethyl esters remain unaffected. Less reactive compounds are discussed in terms of steric factors, and yields are increased by altering the azide solvation.

Original language	English (US)
Pages (from-to)	2477-2479
Number of pages	3
Journal	Organic Letters
Volume	3
Issue number	16
DOIs	https://doi.org/10.1021/ol016104b
State	Published - Aug 9 2001

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol016104b

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abstract = "matrix presented A mild and selective cleavage of p-nitrobenzoic esters by sodium azide in methanol is reported. This new methodology is mild enough for use with acid-or base-sensitive compounds. No elimination byproducts are formed. Fmoc-and trifluoroacetyl-amino protecting groups, benzyl esters, and ethyl esters remain unaffected. Less reactive compounds are discussed in terms of steric factors, and yields are increased by altering the azide solvation.",

author = "G{\'o}mez-Vidal, {Jos{\'e} A.} and Forrester, {Michael T.} and Silverman, {Richard B.}",

year = "2001",

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journal = "Organic Letters",

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T1 - Mild and selective sodium azide mediated cleavage of p-nitrobenzoic esters

AU - Gómez-Vidal, José A.

AU - Forrester, Michael T.

AU - Silverman, Richard B.

PY - 2001/8/9

Y1 - 2001/8/9

N2 - matrix presented A mild and selective cleavage of p-nitrobenzoic esters by sodium azide in methanol is reported. This new methodology is mild enough for use with acid-or base-sensitive compounds. No elimination byproducts are formed. Fmoc-and trifluoroacetyl-amino protecting groups, benzyl esters, and ethyl esters remain unaffected. Less reactive compounds are discussed in terms of steric factors, and yields are increased by altering the azide solvation.

AB - matrix presented A mild and selective cleavage of p-nitrobenzoic esters by sodium azide in methanol is reported. This new methodology is mild enough for use with acid-or base-sensitive compounds. No elimination byproducts are formed. Fmoc-and trifluoroacetyl-amino protecting groups, benzyl esters, and ethyl esters remain unaffected. Less reactive compounds are discussed in terms of steric factors, and yields are increased by altering the azide solvation.

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JO - Organic Letters

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Mild and selective sodium azide mediated cleavage of p-nitrobenzoic esters

Abstract

ASJC Scopus subject areas

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