Aromatic nitration using nitroguanidine and EGDN

Jimmie C. Oxley; James L. Smith; Jesse S. Moran; Jonathan N. Canino; Joseph Almog

doi:10.1016/j.tetlet.2008.04.153

Aromatic nitration using nitroguanidine and EGDN

Jimmie C. Oxley^*, James L. Smith, Jesse S. Moran, Jonathan N. Canino, Joseph Almog

^*Corresponding author for this work

Institute of Chemistry

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

27 Scopus citations

Abstract

Acid catalyzed nitration has been examined using a variety of novel nitration agents: guanidine nitrate (GN) and nitroguanidine (NQ) as well as the simple nitrate ester, ethylene glycol dinitrate (EGDN). Reactions with either activated or deactivated aromatic substrates proceed rapidly and in high yield. Regioselectivity was similar for all nitrating agents examined. The synthetic advantages of liquid EGDN include high solubility in organic solvents, strong nitration activity and ease of preparation.

Original language	English
Pages (from-to)	4449-4451
Number of pages	3
Journal	Tetrahedron Letters
Volume	49
Issue number	28
DOIs	https://doi.org/10.1016/j.tetlet.2008.04.153
State	Published - 7 Jul 2008

Keywords

Aromatic nitration
EGDN
Mixed acid
Regioselectivity

Access to Document

10.1016/j.tetlet.2008.04.153

Cite this

@article{bd5574ea181c4918856f452b80d7e157,

title = "Aromatic nitration using nitroguanidine and EGDN",

abstract = "Acid catalyzed nitration has been examined using a variety of novel nitration agents: guanidine nitrate (GN) and nitroguanidine (NQ) as well as the simple nitrate ester, ethylene glycol dinitrate (EGDN). Reactions with either activated or deactivated aromatic substrates proceed rapidly and in high yield. Regioselectivity was similar for all nitrating agents examined. The synthetic advantages of liquid EGDN include high solubility in organic solvents, strong nitration activity and ease of preparation.",

keywords = "Aromatic nitration, EGDN, Mixed acid, Regioselectivity",

author = "Oxley, {Jimmie C.} and Smith, {James L.} and Moran, {Jesse S.} and Canino, {Jonathan N.} and Joseph Almog",

year = "2008",

month = jul,

day = "7",

doi = "10.1016/j.tetlet.2008.04.153",

language = "אנגלית",

volume = "49",

pages = "4449--4451",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "28",

}

TY - JOUR

T1 - Aromatic nitration using nitroguanidine and EGDN

AU - Oxley, Jimmie C.

AU - Smith, James L.

AU - Moran, Jesse S.

AU - Canino, Jonathan N.

AU - Almog, Joseph

PY - 2008/7/7

Y1 - 2008/7/7

N2 - Acid catalyzed nitration has been examined using a variety of novel nitration agents: guanidine nitrate (GN) and nitroguanidine (NQ) as well as the simple nitrate ester, ethylene glycol dinitrate (EGDN). Reactions with either activated or deactivated aromatic substrates proceed rapidly and in high yield. Regioselectivity was similar for all nitrating agents examined. The synthetic advantages of liquid EGDN include high solubility in organic solvents, strong nitration activity and ease of preparation.

AB - Acid catalyzed nitration has been examined using a variety of novel nitration agents: guanidine nitrate (GN) and nitroguanidine (NQ) as well as the simple nitrate ester, ethylene glycol dinitrate (EGDN). Reactions with either activated or deactivated aromatic substrates proceed rapidly and in high yield. Regioselectivity was similar for all nitrating agents examined. The synthetic advantages of liquid EGDN include high solubility in organic solvents, strong nitration activity and ease of preparation.

KW - Aromatic nitration

KW - EGDN

KW - Mixed acid

KW - Regioselectivity

UR - http://www.scopus.com/inward/record.url?scp=44649171572&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2008.04.153

DO - 10.1016/j.tetlet.2008.04.153

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:44649171572

SN - 0040-4039

VL - 49

SP - 4449

EP - 4451

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 28

ER -

Aromatic nitration using nitroguanidine and EGDN

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this