NITRATION OF CYCLOPENTENECARBOXALDEHYDE : STUDIES TOWARD 1-AMINO-2-NITROCYCLOPENTANECARBOXYLIC ACID

Chase C. Smith; John M. Jacyno; Kendra K. Zeiter; Paul D. Parkanzky; Chad E. Paxson; Peter Pekelnicky; John S. Harwood; Allen D. Hunter; Vincent G. Lucarelli; Michael W. Lufaso; Horace G. Cutler

doi:10.1016/S0040-4039(98)01402-6

NITRATION OF CYCLOPENTENECARBOXALDEHYDE : STUDIES TOWARD 1-AMINO-2-NITROCYCLOPENTANECARBOXYLIC ACID

Chase C. Smith, John M. Jacyno, Kendra K. Zeiter, Paul D. Parkanzky, Chad E. Paxson, Peter Pekelnicky, John S. Harwood, Allen D. Hunter, Vincent G. Lucarelli, Michael W. Lufaso, Horace G. Cutler

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

Abstract

The formation of 2,2-dinitrocyclopentanone oxime is described during an attempted nitroacetamidation of cyclopentenecarboxaldehyde using ceric ammonium nitrate and sodium nitrite in acetonitrile. Progress towards the total synthesis of 1-amino-2-nitrocyclopentanecarboxylic acid is also discussed.
The formation of 2,2-dinitrocyclopentanone oxime is described during an attempted nitroacetamidation of cyclopentenecarboxylic acid.

Original language	American English
Journal	Tetrahedron Letters
Volume	39
DOIs	https://doi.org/10.1016/S0040-4039(98)01402-6
State	Published - Sep 1 1998
Externally published	Yes

Keywords

Aldehydes
Decarbonylation
Nitro compounds
Oximes

Disciplines

Organic Chemistry
Inorganic Chemistry
Chemistry

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@article{3eee7659a96f494bb002b9538cd14e92,

title = "NITRATION OF CYCLOPENTENECARBOXALDEHYDE : STUDIES TOWARD 1-AMINO-2-NITROCYCLOPENTANECARBOXYLIC ACID",

abstract = "The formation of 2,2-dinitrocyclopentanone oxime is described during an attempted nitroacetamidation of cyclopentenecarboxaldehyde using ceric ammonium nitrate and sodium nitrite in acetonitrile. Progress towards the total synthesis of 1-amino-2-nitrocyclopentanecarboxylic acid is also discussed. The formation of 2,2-dinitrocyclopentanone oxime is described during an attempted nitroacetamidation of cyclopentenecarboxylic acid.",

keywords = "Aldehydes, Decarbonylation, Nitro compounds, Oximes",

author = "Smith, \{Chase C.\} and Jacyno, \{John M.\} and Zeiter, \{Kendra K.\} and Parkanzky, \{Paul D.\} and Paxson, \{Chad E.\} and Peter Pekelnicky and Harwood, \{John S.\} and Hunter, \{Allen D.\} and Lucarelli, \{Vincent G.\} and Lufaso, \{Michael W.\} and Cutler, \{Horace G.\}",

note = "The formation of 2,2-dinitrocyclopentanone oxime is described during an attempted nitroacetamidation of cyclopentenecarboxaldehyde using ceric ammonium nitrate and sodium nitrite in acetonitrile. Progress towards the total synthesis of 1-amino-2-nitrocyclopentanecarboxylic acid is also discussed.",

year = "1998",

month = sep,

day = "1",

doi = "10.1016/S0040-4039(98)01402-6",

language = "American English",

volume = "39",

journal = "Tetrahedron Letters",

issn = "0040-4039",

}

TY - JOUR

T1 - NITRATION OF CYCLOPENTENECARBOXALDEHYDE : STUDIES TOWARD 1-AMINO-2-NITROCYCLOPENTANECARBOXYLIC ACID

AU - Smith, Chase C.

AU - Jacyno, John M.

AU - Zeiter, Kendra K.

AU - Parkanzky, Paul D.

AU - Paxson, Chad E.

AU - Pekelnicky, Peter

AU - Harwood, John S.

AU - Hunter, Allen D.

AU - Lucarelli, Vincent G.

AU - Lufaso, Michael W.

AU - Cutler, Horace G.

N1 - The formation of 2,2-dinitrocyclopentanone oxime is described during an attempted nitroacetamidation of cyclopentenecarboxaldehyde using ceric ammonium nitrate and sodium nitrite in acetonitrile. Progress towards the total synthesis of 1-amino-2-nitrocyclopentanecarboxylic acid is also discussed.

PY - 1998/9/1

Y1 - 1998/9/1

N2 - The formation of 2,2-dinitrocyclopentanone oxime is described during an attempted nitroacetamidation of cyclopentenecarboxaldehyde using ceric ammonium nitrate and sodium nitrite in acetonitrile. Progress towards the total synthesis of 1-amino-2-nitrocyclopentanecarboxylic acid is also discussed. The formation of 2,2-dinitrocyclopentanone oxime is described during an attempted nitroacetamidation of cyclopentenecarboxylic acid.

AB - The formation of 2,2-dinitrocyclopentanone oxime is described during an attempted nitroacetamidation of cyclopentenecarboxaldehyde using ceric ammonium nitrate and sodium nitrite in acetonitrile. Progress towards the total synthesis of 1-amino-2-nitrocyclopentanecarboxylic acid is also discussed. The formation of 2,2-dinitrocyclopentanone oxime is described during an attempted nitroacetamidation of cyclopentenecarboxylic acid.

KW - Aldehydes

KW - Decarbonylation

KW - Nitro compounds

KW - Oximes

UR - http://www.sciencedirect.com/science/article/pii/S0040403998014026

U2 - 10.1016/S0040-4039(98)01402-6

DO - 10.1016/S0040-4039(98)01402-6

M3 - Article

SN - 0040-4039

VL - 39

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -

NITRATION OF CYCLOPENTENECARBOXALDEHYDE : STUDIES TOWARD 1-AMINO-2-NITROCYCLOPENTANECARBOXYLIC ACID

Abstract

Keywords

Disciplines

Access to Document

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