Rearrangement of Arylsulfamates and Sulfates to Para-Sulfonyl Anilines and Phenols
Abstract
1. Introduction
2. Results and Discussion
3. Control Experiments
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Entry | Eq. | T (°C) | Atmosphere | Solvent | p-4a at t = 2 h (%) a | p-4a at t = 24 h (%) a | Selectivity p:o a |
---|---|---|---|---|---|---|---|
1 | 0.5 | 101 | Ar | 1,4-Dioxane | 6 | 7 | - |
2 | 1.0 | 101 | Ar | 1,4-Dioxane | 1 | 6 | - |
3 | 1.5 | 101 | Ar | 1,4-Dioxane | 7 | 10 | - |
4 | 2 | 101 | Ar | 1,4-Dioxane | 4 | 12 | - |
5 | 4 | 101 | Ar | 1,4-Dioxane | 4 | 9 | - |
6 | 2 | 101 | air | 1,4-Dioxane | 3 | 11 | - |
7 b | 2 | 80 | Ar | 1,4-Dioxane | - | - | - |
8 | 2 | 100 | Ar | Formic Acid | - | - | - |
9 | 2 | 100 | Ar | Butan-2-ol | - | - | - |
10 | 2 | 80 | Ar | DMF | - | - | - |
11 | 2 | 100 | Ar | DMF | 4 | 13 | - |
12 | 2 | 120 | Ar | DMF | 32 | 58 | >10:1 |
13 | 2 | 140 | Ar | DMF | 30 | 49 | 5:1 |
14 | 2 | 120 | Ar | DMSO | 25 | 48 | 8:1 |
15 | 2 | 140 | Ar | DMSO | 15 | 35 | 2:1 |
16 | 2 | 160 | Ar | DMSO | - | - | - |
17 | 2 | 180 | Ar | DMSO | - | - | - |
18 | 2 | 120 | Ar | 1,2-dichlorobenzene | 27 | 52 | >10:1 |
19 | 2 | 140 | Ar | 1,2-dichlorobenzene | 20 | 44 | 4:1 |
20 c | 2 | 160 | Ar | 1,2-dichlorobenzene | - | - | - |
21 c | 2 | 180 | Ar | 1,2-dichlorobenzene | - | - | - |
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Zhou, Y.; Jones, A.M. Rearrangement of Arylsulfamates and Sulfates to Para-Sulfonyl Anilines and Phenols. Molecules 2024, 29, 1445. https://doi.org/10.3390/molecules29071445
Zhou Y, Jones AM. Rearrangement of Arylsulfamates and Sulfates to Para-Sulfonyl Anilines and Phenols. Molecules. 2024; 29(7):1445. https://doi.org/10.3390/molecules29071445
Chicago/Turabian StyleZhou, Yifei, and Alan M. Jones. 2024. "Rearrangement of Arylsulfamates and Sulfates to Para-Sulfonyl Anilines and Phenols" Molecules 29, no. 7: 1445. https://doi.org/10.3390/molecules29071445
APA StyleZhou, Y., & Jones, A. M. (2024). Rearrangement of Arylsulfamates and Sulfates to Para-Sulfonyl Anilines and Phenols. Molecules, 29(7), 1445. https://doi.org/10.3390/molecules29071445