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Efficient Preparation of Nitrosoarenes for the Synthesis of Azobenzenes
Abstract
[reaction: see text] Reaction conditions are described for the oxidation of anilines furnishing nitrosoarenes and the synthesis of unsymmetrically substituted azobenzenes. In a comparative study, the catalytic oxidation of methyl 4-aminobenzoate by hydrogen peroxide was investigated, and SeO(2) proved to be superior or equal to methyl trioxorhenium (MTO) and Na(2)WO(4), respectively. Nevertheless, the application of the inexpensive, environmentally friendly, Oxone in a biphasic system proved to be more efficient, and a variety of useful nitrosoarenes for the synthesis of azo compounds were prepared in high yield and purity on a large scale.
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Cited by
Azobenzene-based solar thermal fuels: design, properties, and applications
Dong, L., Feng, Y., Wang, L., & Feng, W. (2018) · Chemical Society Reviews · doi:10.1039/c8cs00470f · Cited by 474
ortho‐Fluoroazobenzenes: Visible Light Switches with Very Long‐Lived Z Isomers
Knie, C., Utecht, M., Zhao, F., Kulla, H., Kovalenko, S., Brouwer, A. M., Saalfrank, P., Hecht, S., & Bléger, D. (2014) · Chemistry – A European Journal · doi:10.1002/chem.201404649 · Cited by 438
Castro-Falcón, G., Millán-Aguiñaga, N., Roullier, C., Jensen, P. R., & Hughes, C. C. (2018) · ACS Chemical Biology · doi:10.1021/acschembio.8b00598 · Cited by 29
Metadata
- Authors
- Priewisch, B., & Rück-Braun, K.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-02-11
- Volume
- 70
- Issue
- 6
- Pages
- 2350-2352
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2120471503
- Cited by
- 232
- References
- 0
- FWCI
- 4.37
- Type
- journal article
- Language
- en
- Open access
- closed
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- Priewisch, B., & Rück-Braun, K. (2005). Efficient Preparation of Nitrosoarenes for the Synthesis of Azobenzenes. The Journal of Organic Chemistry. https://doi.org/10.1021/jo048544x
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