Metal-free, room temperature, acid-K2S2O8 mediated method for the nitration of olefins: an easy approach for the synthesis of nitroolefins

Here, we have developed a simple, room temperature method for the nitration of olefins by using inexpensive sodium nitrite as a source of nitro groups in the presence of trifluoroacetic acid (TFA) and potassium persulfate (K2S2O8) under an open atmosphere. Styrenes and mono-substituted olefins give...

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Bibliographic Details
Published in:RSC advances 2019-09, Vol.9 (52), p.30428-30431
Main Authors: Ambala, Srinivas, Singh, Rohit, Singh, Maninder, Pankaj Singh Cham, Gupta, Ria, Munagala, Gurunadham, Kushalava Reddy Yempalla, Vishwakarma, Ram A, Parvinder Pal Singh
Format: Article
Language:English
Subjects:
Alkenes
Chemistry
Mass spectra
Nitration
NMR
Nuclear magnetic resonance
Potassium persulfate
Room temperature
Sodium nitrite
Styrenes
Substitutes
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Summary:Here, we have developed a simple, room temperature method for the nitration of olefins by using inexpensive sodium nitrite as a source of nitro groups in the presence of trifluoroacetic acid (TFA) and potassium persulfate (K2S2O8) under an open atmosphere. Styrenes and mono-substituted olefins give stereo-selective corresponding E-nitroolefins under optimized conditions, however, 1,1-bisubstituted olefins give a mixture of E- and Z-nitroolefins. The optimized conditions work well with electron-donating, electron-withdrawing, un-substituted and heterocyclic styrenes and mono-substituted olefins and give corresponding nitroolefins with good to excellent yields.
ISSN:2046-2069
DOI:10.1039/c9ra06414a