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Improved Arndt-Eistert synthesis of alpha-diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger

(2010) JOURNAL OF ORGANIC CHEMISTRY. 75(16). p.5760-5763
Author
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

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MLA
Pace, Vittorio, Guido Verniest, Josep-Vicent Sinisterra, 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 75.16 (2010): 5760–5763. Print.
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.
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): 5760–5763.
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.
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://dx.doi.org/10.1021/jo101105g},
  volume       = {75},
  year         = {2010},
}

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