Electrophilic Tetraalkylammonium Nitrate Nitration. II. Improved Anhydrous Aromatic and Heteroaromatic Mononitration with Tetramethylammonium Nitrate and Triflic Anhydride, Including Selected Microwave Examples

A new one-pot nitration employing tetramethylammonium nitrate and trifluoromethanesulfonic anhydride in dichloromethane to provide a ready source of the nitronium triflate nitrating agent is presented. Rapid and selective nitration with a variety of aromatic and heteroaromatic substrates is achieved...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2003-01, Vol.68 (2), p.267-275
Main Authors: Shackelford, Scott A, Anderson, Mark B, Christie, Lance C, Goetzen, Thomas, Guzman, Mark C, Hananel, Martha A, Kornreich, Wayne D, Li, Haitao, Pathak, Ved P, Rabinovich, Alex K, Rajapakse, Ranjan J, Truesdale, Larry K, Tsank, Stella M, Vazir, Haresh N
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A new one-pot nitration employing tetramethylammonium nitrate and trifluoromethanesulfonic anhydride in dichloromethane to provide a ready source of the nitronium triflate nitrating agent is presented. Rapid and selective nitration with a variety of aromatic and heteroaromatic substrates is achieved resulting in the synthesis of several novel organic compounds. A distinct advantage is the removal of undesired byproducts by aqueous workup. This very mild nitration permits large-scale syntheses and gives high isolated product yields that often require no further purification. This tetramethylammonium nitrate-based nitration also has been applied to microwave-assisted conditions, and the results with several compounds are outlined.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo026202q