Microwave-assisted reactions are an environmentally
friendly approach for synthesizing organic compounds. In this study, oximation
of acetylferrocene and acetophenone was conducted under both microwave irradiation
and conventional heating conditions. Acetylferrocene and acetophenone were
subjected to oximation under the two conditions in various solvent mixtures,
and the extent of conversion was determined by 1H nuclear magnetic
resonance spectroscopy. Microwave irradiation was found to accelerate the rate of
oximation of both acetylferrocene and acetophenone. Acceleration of the
reaction under microwave irradiation was attributed to the efficient absorption
of microwaves by the ferrocene nucleus.
References
[1]
Colacino, E., Dayaker, G., Morere, A. and Friscic, T. (2019) Introducing Students to Mechanochemistry via Environmentally Friendly Organic Synthesis Using a Solvent-Free Mechanochemical Preparation of the Antidiabetic Drug Tolbutamide. Journal of Chemical Education, 96, 766-771. https://doi.org/10.1021/acs.jchemed.8b00459
[2]
Coppock, P., Park, S.H., Paredes, J., Pennington, R., Pursell, D.P., Rudd, G., Sloop, J.C. and Tsoi, M.Y. (2017) Enhancing Research Skills and Attitudes in Undergraduate Organic Chemistry with a Course-Embedded Undergraduate Research Experience (CURE) via Green Organic Synthesis. Journal of Laboratory Chemical Education, 5, 41-47. http://article.sapub.org/10.5923.j.jlce.20170503.01.html
[3]
Ilia, G., Iliescu, S. and Popa, A. (2015) Polymer-Supported Phase Transfer Catalysts in Green Organic Syntheses. Current Green Chemistry, 2, 264-273. https://doi.org/10.2174/2213346102999150306112846
[4]
Sowmiah, S., Cheng, C.I. and Chu, Y. (2012) Ionic Liquids for Green Organic Synthesis. Current Organic Synthesis, 9, 74-95. https://doi.org/10.2174/157017912798889116
[5]
Leveque, J. and Cravotto, G. (2006) Microwaves, Power Ultrasound, and Ionic Liquids. A New Synergy in Green Organic Synthesis. Chimia, 60, 313-320. https://doi.org/10.2533/000942906777836255
[6]
Giguere, R., Bray, T., Duncan, S.M. and Majetich, G. (1986) Application of Commercial Microwave Ovens to Organic Synthesis. Tetrahedron Letters, 27, 4945-4948. https://doi.org/10.1016/S0040-4039(00)85103-5
[7]
Mancini, P.M.E., Kneeteman, M.N., Cainelli, M., Ormachea, C.M. and Domingo, L.R. (2017) Nitropyrroles, Diels-Alder Reactions Assisted by Microwave Irradiation and solvent Effect. An Experimental and Theoretical Study. Journal of Molecular Structure, 1147, 155-160. https://doi.org/10.1016/j.molstruc.2017.06.109
[8]
Du, C., Zhang, J., Li, L., Wang, K. and Luo, G. (2019) A Modified Mixed-Acid Catalytic System for Beckmann Rearrangement of Cyclohexanone Oxime. AIChE Journal, 65, e16603 https://doi.org/10.1002/aic.16603
[9]
Lee, H. and Kim, H. (2014) Novel Fluorescent Probe for the Selective Detection of Organophosphorous Nerve Agents through a Cascade Reaction from Oxime to Nitrile via Isoxazole. Tetrahedron, 70, 2966-2970. https://doi.org/10.1016/j.tet.2014.03.026
[10]
Hayashi, T., Okada, Y. and Hukuchi, T. (1994) The Oxidative Decomposition Reaction of Acylferrocenes under Acidic Conditions. Nippon Kagaku Kaishi, No. 4, 340-344. https://doi.org/10.1246/nikkashi.1994.340
[11]
Gao, Z., Zhang, J., Zhang, S., Lan, D., Zhao, Z. and Kou, K. (2020) Strategies for Electromagnetic Wave Absorbers Derived from Zeolite Imidazole Framework (ZIF-67) with Ferrocene Containing Polymers. Polymer, 202, 122679. https://doi.org/10.1016/j.polymer.2020.122679
[12]
Ge, C., Zou, J., Yan, M. and Bi, H. (2014) C-Dots Induced Microwave Absorption Enhancement of PANI/Ferrocene/C-Dots. Materials Letters, 137, 41-44. https://doi.org/10.1016/j.matlet.2014.08.111.