Improved Arndt-Eistert synthesis of alpha-diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger
- Author
- Vittorio Pace, Guido Verniest (UGent) , Josep-Vicent Sinisterra, Andrés R Alcántara and Norbert De Kimpe (UGent)
- Organization
- Abstract
- A practical methodology to obtain alpha-diazoketones through an improved Arndt-Eistert synthesis is described. The method allows the efficient transformation of acid halides using a stoichiometric amount of diazomethane in the presence of calcium oxide, without concomitant ketene or haloketone formation. The obtained alpha'-brominated-alpha-diazoketones were employed as suitable substrates for the synthesis of interesting alpha-arylamino-alpha'-halomethylketones.
- Keywords
- DIAZO-KETONES, H INSERTION REACTIONS, DIAZOCARBONYL COMPOUNDS, ORGANIC-SYNTHESIS, BETA-LACTAMS, TRIMETHYLSILYLDIAZOMETHANE, REAGENT, DERIVATIVES, ACETOLYSIS, CONVERSION
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-1257993
- MLA
- Pace, Vittorio, et al. “Improved Arndt-Eistert Synthesis of Alpha-Diazoketones Requiring Minimal Diazomethane in the Presence of Calcium Oxide as Acid Scavenger.” JOURNAL OF ORGANIC CHEMISTRY, vol. 75, no. 16, 2010, pp. 5760–63, doi:10.1021/jo101105g.
- APA
- Pace, V., Verniest, G., Sinisterra, J.-V., Alcántara, A. R., & De Kimpe, N. (2010). Improved Arndt-Eistert synthesis of alpha-diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger. JOURNAL OF ORGANIC CHEMISTRY, 75(16), 5760–5763. https://doi.org/10.1021/jo101105g
- Chicago author-date
- Pace, Vittorio, Guido Verniest, Josep-Vicent Sinisterra, Andrés R Alcántara, and Norbert De Kimpe. 2010. “Improved Arndt-Eistert Synthesis of Alpha-Diazoketones Requiring Minimal Diazomethane in the Presence of Calcium Oxide as Acid Scavenger.” JOURNAL OF ORGANIC CHEMISTRY 75 (16): 5760–63. https://doi.org/10.1021/jo101105g.
- Chicago author-date (all authors)
- Pace, Vittorio, Guido Verniest, Josep-Vicent Sinisterra, Andrés R Alcántara, and Norbert De Kimpe. 2010. “Improved Arndt-Eistert Synthesis of Alpha-Diazoketones Requiring Minimal Diazomethane in the Presence of Calcium Oxide as Acid Scavenger.” JOURNAL OF ORGANIC CHEMISTRY 75 (16): 5760–5763. doi:10.1021/jo101105g.
- Vancouver
- 1.Pace V, Verniest G, Sinisterra J-V, Alcántara AR, De Kimpe N. Improved Arndt-Eistert synthesis of alpha-diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger. JOURNAL OF ORGANIC CHEMISTRY. 2010;75(16):5760–3.
- IEEE
- [1]V. Pace, G. Verniest, J.-V. Sinisterra, A. R. Alcántara, and N. De Kimpe, “Improved Arndt-Eistert synthesis of alpha-diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger,” JOURNAL OF ORGANIC CHEMISTRY, vol. 75, no. 16, pp. 5760–5763, 2010.
@article{1257993,
abstract = {{A practical methodology to obtain alpha-diazoketones through an improved Arndt-Eistert synthesis is described. The method allows the efficient transformation of acid halides using a stoichiometric amount of diazomethane in the presence of calcium oxide, without concomitant ketene or haloketone formation. The obtained alpha'-brominated-alpha-diazoketones were employed as suitable substrates for the synthesis of interesting alpha-arylamino-alpha'-halomethylketones.}},
author = {{Pace, Vittorio and Verniest, Guido and Sinisterra, Josep-Vicent and Alcántara, Andrés R and De Kimpe, Norbert}},
issn = {{0022-3263}},
journal = {{JOURNAL OF ORGANIC CHEMISTRY}},
keywords = {{DIAZO-KETONES,H INSERTION REACTIONS,DIAZOCARBONYL COMPOUNDS,ORGANIC-SYNTHESIS,BETA-LACTAMS,TRIMETHYLSILYLDIAZOMETHANE,REAGENT,DERIVATIVES,ACETOLYSIS,CONVERSION}},
language = {{eng}},
number = {{16}},
pages = {{5760--5763}},
title = {{Improved Arndt-Eistert synthesis of alpha-diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger}},
url = {{http://doi.org/10.1021/jo101105g}},
volume = {{75}},
year = {{2010}},
}
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