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Please login to access the full content or check if you have access via34.6.1.2.1 Method 1: Fluorination of Alkylbenzenes with Cesium Fluoroxysulfate
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Sai Krishna Murthy, A.; Tardivel, R.; Grée, R., Science of Synthesis, (2005) 34, 313.
The fluorination of mono-, di-, and trimethyl-substituted benzenes 84 is possible with cesium fluoroxysulfate in acetonitrile. In the case of monosubstituted benzenes, the highest conversions of starting material into fluoro-substituted products 85 and 86 are achieved when 0.5 M solutions of alkyl-substituted aromatic derivatives in acetonitrile are treated with a 60% molar excess of cesium fluoroxysulfate in the absence of oxygen. As shown in Table 1, side-chain fluoro functionalizations (e.g., to give 85) are predominant, if not the exclusive process (entries 1–5).[50] In most of the disubstituted methylbenzene derivatives the benzylic fluoro functionalization is also a predominant process on reaction with cesium fluoroxysulfate (entries 6–8). However, complex mixtures of regioisomers are obtained in the case of the trimethylbenzenes (entries 9–11).
Meeee 8 Meeeeeeeeeee ee Meeeeeeeeeeee eeee Meeeee Meeeeeeeeeeeeee[88]
Meeee | M8 | M8 | M8 | M8 | M8 | M8 | M8 | Meeee (88/88) | Meeee (%) | Mee |
---|---|---|---|---|---|---|---|---|---|---|
8 | M | M | M | M | M | M | M | 88:88 | 88 | [88] |
8 | M | Me | M | M | M | M | M | 888:eeeee | 88 | [88] |
8 | Me | Me | M | M | M | M | M | 888:eeeee | 88 | [88] |
8 | M | Me | M | M | M | M | M | 88:88 | 88 | [88] |
8 | Me | Me | M | M | M | M | M | 888:eeeee | 88 | [88] |
8 | M | M | Me | M | M | M | M | 88:88 | 88 | [88] |
8 | M | M | M | Me | M | M | M | 88:88 | 88 | [88] |
8 | M | M | M | M | Me | M | M | 88:88 | 88 | [88] |
8 | M | M | Me | Me | M | M | M | 88:88 | 88 | [88] |
88 | M | M | Me | M | Me | M | M | 88:88 | 88 | [88] |
88 | M | M | M | Me | M | Me | M | 88:88 | 88 | [88] |
Meeeeeeeeeee Meeeeeeee
Meeeee Meeeeeee (88, M8 = M8 = M8 = M8 = M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeee eeeeeeeeeeeeeee eee e eee eeeeeeeee; eeeeeeeee eeeeee eeeeee eeeeeeeeeee eeeeee ee eeeee eeeeee eee eeeeeee eee eeeeeeee; eee eeeeeeeee eeee ee ee eeeeeee eee eeeee e eeee-eeeeeeeeee eeee eee eee eeeeeee ee eeee eeeeeee eeee e eeeeeeee eeeeeee ee eeeeeeeeee eeeeeeee eeee ee eeeeeee eeeee eeeeeeeeeeeee ee eeee ee eeeeeeeee eee eeee eeeee.
M eeee ee eeeeeee (8.888 e, 8 eeee) ee eee, eeeeeee eeeeeeeee MeMM (8 eM) eee eeeeeeee eeee eee M8-eeee M8. Meee, MeMM8M (8.8 e, 8.8 eeee) eee eeeeeeeeee eee eee eeeeeee eee eeeeeee eeeee M8 ee 88–88°M eee 8 e eee eeeeeee eeee MM8Me8 (88 eM). Mee eeeeeeeee eeeeeee eee eeeeeee ee eeeeeeeeee, eee eeeeeeee eee eeeeee eeee M8M (88 eM) eee eeeee (Me8MM8), eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Meeeee eeeeeeee eee eeeeeeee ee e eeeeee ee eeeeeeeeeee MMM; eeeee: 8.888 e (88%).
References
[50] | Meeeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 88.