Polyunsaturated nitroalkanes and nitro-substituted fatty acids

C. J. Easton; L. Xia; M. J. Pitt; A. Ferrante; A. Poulos; D. A. Rathjen

doi:10.1055/s-2001-11433

Polyunsaturated nitroalkanes and nitro-substituted fatty acids

C. J. Easton^*, L. Xia, M. J. Pitt, A. Ferrante, A. Poulos, D. A. Rathjen

^*Corresponding author for this work

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

17 Citations (Scopus)

Abstract

Nitroalkanes 4 are readily prepared from naturally derived polyunsaturated fatty alcohols 1 via succesive conversion to the corresponding haloalkanes 2 and 3, and reaction with silver nitrite. Reaction of nitroalkanes 4a,b with methyl acrylate, followed by ester hydrolysis, affords nitro-substituted fatty acids 6a,b and 8a,b. Oxidation of alcohols 1a,b gives the corresponding aldehydes 9a,b, which react by Henry condensation with nitromethane to give β-hydroxynitroalkanes 10a,b.

Original language	English
Pages (from-to)	451-457
Number of pages	7
Journal	Synthesis
Issue number	3
DOIs	https://doi.org/10.1055/s-2001-11433
Publication status	Published - 2001

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title = "Polyunsaturated nitroalkanes and nitro-substituted fatty acids",

abstract = "Nitroalkanes 4 are readily prepared from naturally derived polyunsaturated fatty alcohols 1 via succesive conversion to the corresponding haloalkanes 2 and 3, and reaction with silver nitrite. Reaction of nitroalkanes 4a,b with methyl acrylate, followed by ester hydrolysis, affords nitro-substituted fatty acids 6a,b and 8a,b. Oxidation of alcohols 1a,b gives the corresponding aldehydes 9a,b, which react by Henry condensation with nitromethane to give β-hydroxynitroalkanes 10a,b.",

keywords = "Carboxylic acids, Henry reactions, Lipids, Michael additions, Nitroalkanes",

author = "Easton, {C. J.} and L. Xia and Pitt, {M. J.} and A. Ferrante and A. Poulos and Rathjen, {D. A.}",

year = "2001",

doi = "10.1055/s-2001-11433",

language = "English",

pages = "451--457",

journal = "Synthesis",

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T1 - Polyunsaturated nitroalkanes and nitro-substituted fatty acids

AU - Easton, C. J.

AU - Xia, L.

AU - Pitt, M. J.

AU - Ferrante, A.

AU - Poulos, A.

AU - Rathjen, D. A.

PY - 2001

Y1 - 2001

N2 - Nitroalkanes 4 are readily prepared from naturally derived polyunsaturated fatty alcohols 1 via succesive conversion to the corresponding haloalkanes 2 and 3, and reaction with silver nitrite. Reaction of nitroalkanes 4a,b with methyl acrylate, followed by ester hydrolysis, affords nitro-substituted fatty acids 6a,b and 8a,b. Oxidation of alcohols 1a,b gives the corresponding aldehydes 9a,b, which react by Henry condensation with nitromethane to give β-hydroxynitroalkanes 10a,b.

AB - Nitroalkanes 4 are readily prepared from naturally derived polyunsaturated fatty alcohols 1 via succesive conversion to the corresponding haloalkanes 2 and 3, and reaction with silver nitrite. Reaction of nitroalkanes 4a,b with methyl acrylate, followed by ester hydrolysis, affords nitro-substituted fatty acids 6a,b and 8a,b. Oxidation of alcohols 1a,b gives the corresponding aldehydes 9a,b, which react by Henry condensation with nitromethane to give β-hydroxynitroalkanes 10a,b.

KW - Carboxylic acids

KW - Henry reactions

KW - Lipids

KW - Michael additions

KW - Nitroalkanes

UR - http://www.scopus.com/inward/record.url?scp=0035100427&partnerID=8YFLogxK

U2 - 10.1055/s-2001-11433

DO - 10.1055/s-2001-11433

M3 - Article

SN - 0039-7881

SP - 451

EP - 457

JO - Synthesis

JF - Synthesis

IS - 3

ER -

Polyunsaturated nitroalkanes and nitro-substituted fatty acids

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