Observation of 1,3-Diketones Formation in the Reaction of Bulky Acyl Chlorides with Methyllithium
Abstract
:1. Introduction
2. Results and Discussion
2.1. The Reaction of Menthylformyl Chloride with Methyllithium
2.2. The Effect of the Reaction Condition on the Yield of 1,3-Dimenthylpropane-1,3-dione
Run | Solvent b | MFC/MeLi c | Temperature (°C) | Yield (%) d |
---|---|---|---|---|
1 | Toluene | 1/1.1 | −78 | 20.7 |
2 | Toluene | 1/1.1 | −5 | 61.3 |
3 | Toluene | 1/1.1 | 0 | 67.1 |
4 | Toluene | 1/1.1 | 25 | 40.5 |
5 | Toluene | 1/1.1 | 50 | 22.6 |
6 | Toluene | 1/1 | 0 | 65.2 |
7 | Toluene | 1/2.1 | 0 | 67.0 |
8 | Toluene | 1/3.1 | 0 | 67.1 |
9 e | Toluene | 1/1.1 | 0 | 57.4 |
10 | Tetrahydrofuran | 1/1.1 | 0 | 62.5 |
11 | Diethyl ether | 1/1.1 | 0 | 60.2 |
2.3. The Effect of the Bulk of Group Linking to Carbonyl of Acyl Chloride on the Reaction
Run | R | Yield/% b | ||
---|---|---|---|---|
A | B | C | ||
1 | - | 67.0 | - | |
2 | - | 34.0 | 36.1 | |
3 c | 7.9 | 49.9 | 21.6 | |
4 | - | 10.2 | 84.1 | |
5 d | - | - | 91.1 | |
6 | 69.4 | 12.2 | - |
3. Experimental
3.1. Instruments and Materials
3.2. The Typical Reaction Process
3.3. Chromatographic Eluents and Characterization of the Products
4. Conclusions
Acknowledgments
References and Notes
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Zhang, J.; Yang, N.; Yang, L. Observation of 1,3-Diketones Formation in the Reaction of Bulky Acyl Chlorides with Methyllithium. Molecules 2012, 17, 6415-6423. https://doi.org/10.3390/molecules17066415
Zhang J, Yang N, Yang L. Observation of 1,3-Diketones Formation in the Reaction of Bulky Acyl Chlorides with Methyllithium. Molecules. 2012; 17(6):6415-6423. https://doi.org/10.3390/molecules17066415
Chicago/Turabian StyleZhang, Jian, Nianfa Yang, and Liwen Yang. 2012. "Observation of 1,3-Diketones Formation in the Reaction of Bulky Acyl Chlorides with Methyllithium" Molecules 17, no. 6: 6415-6423. https://doi.org/10.3390/molecules17066415