Electrophilic trifluoromethylation of simple inorganic salts: a one step route to trifluoromethylnitromethane, CF3NO2

Muralidharan, K.; Chakraborty, Rupak; Shreeve, Jean’ne M.

doi:10.1016/j.jfluchem.2004.07.005

Cited by 9 publications

(3 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Shreeve and co-workers demonstrated that trifluoromethylnitromethane can be readily synthesised in 90% yield from the electrophilic trifluoromethylation of sodium nitrite (Scheme 37) [108].…”

Section: Trifluoromethylchalcogen Saltsmentioning

confidence: 99%

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

Ma¹,

Cahard²

2007

Journal of Fluorine Chemistry

543

177

View full text Add to dashboard Cite

Section: Trifluoromethylchalcogen Saltsmentioning

confidence: 99%

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

Ma¹,

Cahard²

2007

Journal of Fluorine Chemistry

543

177

View full text Add to dashboard Cite

“…As the two vital parameters of energetic compounds, the detonation velocity (km·s -1 ) and detonation pressure of the title compounds were calculated using the empirical Kamlet−Jacobs (K-J) equations [59]:…”

Section: Methodsmentioning

confidence: 99%

Theoretical study on novel nitrogen-rich energetic compounds of bis(amino)-azobis(azoles) with tetrazene unit

Zeng

Zhang

et al. 2012

J Mol Model

View full text Add to dashboard Cite

Six stereoisomers of 5,5'-bis(amino)-1,1'-azobis (tetrazoles) and 30 other structures, including all possible bis(amino)-azobis(azoles) with an N−N0N−N unit, were designed. The molecular geometries were fully optimized at the DFT-B3LYP level with the 6-31++g (d, p) basis set. From the absence of any imaginary frequency in the infrared vibration frequency spectrum, it is predicted that all these studied structures may exist in stable forms. The results of the total energies of the stereoisomers of 5,5'-bis(amino)-1,1'-azobis(tetrazoles) indicate that the two symmetric trans-form structures are more likely to exist than the other four. The pyrolysis process, chemical stability and molecular electrostatic potential were studied via the investigation of their electronic structure. Heats of formation (HOFs) were calculated using the atomization energy method based on the results of the harmonic vibration frequencies, and a linear relationship was found between the HOF and nitrogen chain or nitrogen content. Densities of the title compounds were predicted with the Monte Carlo method. Finally, according to the results of the calculated HOFs and densities, the explosive parameters of these compounds were calculated using the Kamlet−Jacobs formula. 5,5'-Bis(amino)-1,1'-azobis(tetrazoles) and its isomer 5,5'-bis (amino)-2,2'-azobis(tetrazoles) may have potential for use as energetic compounds.

show abstract

“…Until recently, these biaryl sulfonium salts have scarcely been used as reagents. Reagents 21 or 22 proved useful for various applications such as the preparation of trifluoromethylated inorganic salts, [30] keto-phosphonamidates, [31] oligofluorenes, [32] pyranones [33] and an iridium complex. These two drawbacks have recently been overcome (vide infra).…”

Section: Sulfonium Saltsmentioning

confidence: 99%

The New Age of Electrophilic Perfluoroalkylation Reactions

2012

View full text Add to dashboard Cite

The introduction of a perfluoroalkyl group, with emphasis on the trifluoromethyl moiety, is a challenging topic. Of the synthetic methods available in the repertoire of chemists, electrophilic introduction was until recently the least developed. In five years, however, a renaissance of this chemistry has happened. This renewal has been made possible thanks to reports both of numerous new reagents (stable, easy tohandle and to prepare) and of easier preparation of older reagents. Their availability rapidly inspired highly original works involving their use, in particular with the help of catalysis. This virtuous spiral, as well as all these exciting new developments, is described in this microreview.

show abstract

Electrophilic trifluoromethylation of simple inorganic salts: a one step route to trifluoromethylnitromethane, CF3NO2

Cited by 9 publications

References 7 publications

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

Theoretical study on novel nitrogen-rich energetic compounds of bis(amino)-azobis(azoles) with tetrazene unit

The New Age of Electrophilic Perfluoroalkylation Reactions

Contact Info

Product

Resources

About

Electrophilic trifluoromethylation of simple inorganic salts: a one step route to trifluoromethylnitromethane, CF3NO2

Cited by 9 publications

References 7 publications

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

Theoretical study on novel nitrogen-rich energetic compounds of bis(amino)-azobis(azoles) with tetrazene unit

The New Age of Electrophilic Perfluoro­alk­ylation Reactions

Contact Info

Product

Resources

About

The New Age of Electrophilic Perfluoroalkylation Reactions