Aromatic nitration using nitroguanidine and EGDN

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 y...

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Bibliographic Details
Published in:Tetrahedron letters 2008-07, Vol.49 (28), p.4449-4451
Main Authors: Oxley, Jimmie C., Smith, James L., Moran, Jesse S., Canino, Jonathan N., Almog, Joseph
Format: Article
Language:English
Subjects:
Aromatic nitration
EGDN
Mixed acid
Regioselectivity
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.04.153