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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