Aromatic Nitration with Nitric Acid/trifluoromethanesulfonic Anhydride

George Andrew Olah; Prakash Reddy; G. K. Surya Prakash

doi:10.1055/s-1992-26310

Aromatic Nitration with Nitric Acid/trifluoromethanesulfonic Anhydride

George Andrew Olah
, Prakash Reddy
, G. K. Surya Prakash

Missouri University of Science and Technology

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

Abstract

Nitric acid/trifluoromethanesulfonic (triflic) anhydride was shown to be a highly effective electrophilic nitrating agent. A series of aromatics were nitrated under mild conditions in high yields. Similar results were also obtained when using nitric acid/trifluoromethanesulfonic acid/phosphorus pentoxide as nitrating agent in nitroethane or nitromethane solution. The ¹⁵ N NMR spectrum of ¹⁵ N enriched nitric acid in triflic anhydride was studied and compared with that of other nitrating reagents. The data indicate the predominantly covalent nature of trifluoromethanesulfonyl nitrate formed in the systems.

Original language	American English
Journal	Synthesis
DOIs	https://doi.org/10.1055/s-1992-26310
State	Published - Nov 1 1992

Keywords

nitro derivative
reaction analysis
synthesis

Disciplines

Chemistry

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https://doi.org/10.1055/s-1992-26310

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title = "Aromatic Nitration with Nitric Acid/trifluoromethanesulfonic Anhydride",

abstract = " Nitric acid/trifluoromethanesulfonic (triflic) anhydride was shown to be a highly effective electrophilic nitrating agent. A series of aromatics were nitrated under mild conditions in high yields. Similar results were also obtained when using nitric acid/trifluoromethanesulfonic acid/phosphorus pentoxide as nitrating agent in nitroethane or nitromethane solution. The 15 N NMR spectrum of 15 N enriched nitric acid in triflic anhydride was studied and compared with that of other nitrating reagents. The data indicate the predominantly covalent nature of trifluoromethanesulfonyl nitrate formed in the systems.",

keywords = "nitro derivative, reaction analysis, synthesis",

author = "Olah, \{George Andrew\} and Prakash Reddy and Prakash, \{G. K. Surya\}",

year = "1992",

month = nov,

day = "1",

doi = "10.1055/s-1992-26310",

language = "American English",

journal = "Synthesis",

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T1 - Aromatic Nitration with Nitric Acid/trifluoromethanesulfonic Anhydride

AU - Olah, George Andrew

AU - Reddy, Prakash

AU - Prakash, G. K. Surya

PY - 1992/11/1

Y1 - 1992/11/1

N2 - Nitric acid/trifluoromethanesulfonic (triflic) anhydride was shown to be a highly effective electrophilic nitrating agent. A series of aromatics were nitrated under mild conditions in high yields. Similar results were also obtained when using nitric acid/trifluoromethanesulfonic acid/phosphorus pentoxide as nitrating agent in nitroethane or nitromethane solution. The 15 N NMR spectrum of 15 N enriched nitric acid in triflic anhydride was studied and compared with that of other nitrating reagents. The data indicate the predominantly covalent nature of trifluoromethanesulfonyl nitrate formed in the systems.

AB - Nitric acid/trifluoromethanesulfonic (triflic) anhydride was shown to be a highly effective electrophilic nitrating agent. A series of aromatics were nitrated under mild conditions in high yields. Similar results were also obtained when using nitric acid/trifluoromethanesulfonic acid/phosphorus pentoxide as nitrating agent in nitroethane or nitromethane solution. The 15 N NMR spectrum of 15 N enriched nitric acid in triflic anhydride was studied and compared with that of other nitrating reagents. The data indicate the predominantly covalent nature of trifluoromethanesulfonyl nitrate formed in the systems.

KW - nitro derivative

KW - reaction analysis

KW - synthesis

UR - https://scholarsmine.mst.edu/chem_facwork/1229

UR - https://doi.org/10.1055/s-1992-26310

U2 - 10.1055/s-1992-26310

DO - 10.1055/s-1992-26310

M3 - Article

JO - Synthesis

JF - Synthesis

ER -

Aromatic Nitration with Nitric Acid/trifluoromethanesulfonic Anhydride

Abstract

Keywords

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