title: Electrophilic tetraalkylammonium nitrate nitration. II. Improved anhydrous aromatic and heteroaromatic mononitration with tetramethylammonium nitrate and triflic anhydride, including selected microwave examples.
abstract: 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.
authors.affiliation: Pfizer Global Research and Development, La Jolla Laboratories, 3550 General Atomics Court, San Diego, California 92121-1194, USA. scott.shackelford@pfizer.com
authors.forename: Scott A
authors.initials: SA
authors.lastname: Shackelford
authors.forename: Mark B
authors.initials: MB
authors.lastname: Anderson
authors.forename: Lance C
authors.initials: LC
authors.lastname: Christie
authors.forename: Thomas
authors.initials: T
authors.lastname: Goetzen
authors.forename: Mark C
authors.initials: MC
authors.lastname: Guzman
authors.forename: Martha A
authors.initials: MA
authors.lastname: Hananel
authors.forename: Wayne D
authors.initials: WD
authors.lastname: Kornreich
authors.forename: Haitao
authors.initials: H
authors.lastname: Li
authors.forename: Ved P
authors.initials: VP
authors.lastname: Pathak
authors.forename: Alex K
authors.initials: AK
authors.lastname: Rabinovich
authors.forename: Ranjan J
authors.initials: RJ
authors.lastname: Rajapakse
authors.forename: Larry K
authors.initials: LK
authors.lastname: Truesdale
authors.forename: Stella M
authors.initials: SM
authors.lastname: Tsank
authors.forename: Haresh N
authors.initials: HN
authors.lastname: Vazir