Azidofluoromethane: synthesis, stability and reactivity in [3 + 2] cycloadditions
Literature Information
Publication Date
2019-11-05
DOI
10.1039/C9QO01295H
Impact Factor
5.281
Authors
Svatava Voltrová, Petr Slavíček, Petr Beier
View Original
Abstract
Azidofluoromethane was prepared for the first time by the nucleophilic displacement of bromofluoromethane with sodium azide. This volatile and unstable compound was isolated by low temperature vacuum distillation with a suitable solvent and fully characterized. Theoretical calculations of its decomposition activation energies and rate constants were performed and the values were compared to those for azidomethane, azidodifluoromethane and azidotrifluoromethane. Azidofluoromethane underwent [3 + 2] cycloadditions with alkynes, 1,3-diones and β-ketoesters to furnish 1-fluoromethyl-1,2,3-triazoles.
Related Literature
Synthesis of azuleno[2,1-b]thiophenes by cycloaddition of azulenylalkynes with elemental sulfur and their structural, optical and electrochemical properties
Taku Shoji, Kota Miura, Akira Ohta, Ryuta Sekiguchi, Shunji Ito, Yuya Endo, Tatsuki Nagahata, Shigeki Mori, Tetsuo Okujima
2019-06-20
Research Article
DOI: 10.1039/C9QO00593E
Ruthenium(ii)-catalyzed selective C–H bond activation of imidamides and coupling with sulfoxonium ylides: an efficient approach for the synthesis of highly functional 3-ketoindoles
Jianhui Zhou, Guoxue He, Huihui Li, Qiaolan Yang, Run Wang, Yu Zhou
2019-02-27
Research Article
DOI: 10.1039/C9QO00048H
A new method for α-specific glucosylation and its application to the one-pot synthesis of a branched α-glucan
Yanxin Zhang, Shihao Zhou, Xiaohan Wang, Han Zhang, Jian Gao
2019-01-30
Research Article
DOI: 10.1039/C8QO01177J
Ruthenium(ii)-catalyzed C–O/C–S cyclization for the synthesis of 5-membered O-containing and S-containing heterocycles
Jian Liu, Yu Wen, Fengjun He, Liang Gao, Lina Gao, Junwei Wang, Xiachang Wang, Yinan Zhang, Lihong Hu
2019-02-06
Research Article
DOI: 10.1039/C8QO01425F
Using light to control the inhibition of Karstedt's catalyst
Brahmjot Kaur, Rameez Raza, Mitchell J. Stashick, Neil R. Branda
2019-03-26
Research Article
DOI: 10.1039/C9QO00221A
Enantiodivergent synthesis of 1,2-bis(diphenylphosphino)ethanes via asymmetric [3 + 2]-cycloaddition
Bing Liu, Wenbo Li, Hai-Hong Wu, Junliang Zhang
2019-01-25
Research Article
DOI: 10.1039/C8QO01404C
Effect of fluorine substitution in organoboron electron acceptors for photovoltaic application
Fangbin Liu, Jun Liu, Lixiang Wang
2019-04-17
Research Article
DOI: 10.1039/C9QO00286C
Copper-catalyzed direct and odorless selenylation with a sodium selenite-based reagent
Yuan Cao, Jie Liu, Fanmin Liu, Lvqi Jiang, Wenbin Yi
2019-01-30
Research Article
DOI: 10.1039/C8QO01355A
Diastereoselective Rh-catalyzed decarboxylative allylation to form quaternary stereocenters using sulfinimine as the directing group
Tongtong Liu, Yunhao Luo, Shende Jiang, Guang Yang
2019-01-24
Research Article
DOI: 10.1039/C8QO01258J
You might also like
Compound Q&A
How should waste containing (6-Bromo-2-naphthyl)oxy](dimethyl)(2-methyl-2-propanyl)silane be handled?
Waste containing (6-Bromo-2-naphthyl)oxy](dimethyl)(2-methyl-2-propanyl)silane (...
100751-65-3[(6-Bromo-2-naphthyl...
Compound Q&A
How is 7-Fluoro-4-isoquinolinecarboxylic acid (CAS: 1841081-40-0) typically synthesized?
7-Fluoro-4-isoquinolinecarboxylic acid can be synthesized via a multi-step proce...
1841081-40-07-Fluoro-4-isoquinol...
Compound Q&A
What are the physical and chemical properties of 2,3,5,6-Tetrabromothieno[3,2-b]thiophene (CAS: 124638-53-5)?
2,3,5,6-Tetrabromothieno[3,2-b]thiophene is a crystalline compound with a high m...
124638-53-52,3,5,6-Tetrabromoth...
Compound Q&A
Is 1-[4-(Benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl]-2-methyl-1H-indole-4-carboxamide (CAS: 1542705-92-9) safe?
1-[4-(Benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl]-2-methyl-1H-indol...
1542705-92-91-[4-(Benzylamino)-7...
Compound Q&A
What is the market or research trend for imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic acid, 3,4-dihydro-3-methyl-4-oxo- (CAS: 113942-30-6)?
The market for imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic acid, 3,4-dihydro-3...
113942-30-6Imidazo[5,1-d]-1,2,3...
Compound Q&A
What is 3-(Triisopropylsilyl)propiolaldehyde (CAS: 163271-80-5)?
3-(Triisopropylsilyl)propiolaldehyde is a synthetic organic compound with the CA...
163271-80-53-(Triisopropylsilyl...
Compound Q&A
What regulatory guidelines apply to 6-Nitro-2H-1,4-benzoxazin-3(4H)-one (CAS: 81721-87-1)?
6-Nitro-2H-1,4-benzoxazin-3(4H)-one (CAS: 81721-87-1) is subject to various regu...
81721-87-16-Nitro-2H-1,4-benzo...
Compound Q&A
How should waste containing (3-Fluorophenyl)(4-{[(2-methyl-2-propanyl)oxy]carbonyl}-1-piperazinyl)acetic acid (CAS: 885272-91-3) be handled?
Waste containing (3-Fluorophenyl)(4-{[(2-methyl-2-propanyl)oxy]carbonyl}-1-piper...
885272-91-3(3-Fluorophenyl)(4-{...
Compound Q&A
What are the physical and chemical properties of N,N'-4,4'-Biphenyldiyldiisonicotinamide (CAS: 55119-40-9)?
N,N'-4,4'-Biphenyldiyldiisonicotinamide is a white crystalline solid with a mole...
55119-40-9N,N'-4,4'-Biphenyldi...
Compound Q&A
What industries use 6-Bromo-8-fluoro-2-quinazolinol (CAS: 1036756-15-6)?
6-Bromo-8-fluoro-2-quinazolinol is primarily used in the pharmaceutical industry...
1036756-15-66-Bromo-8-fluoro-2-q...
Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
2-Methyl-2-propanyl 4-iodo-1-piperidinecarboxylate
CAS Number:
301673-14-3
Molecular Formula:
C10H18INO2
Recommended Suppliers
Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.