Synthesis of the [11]Cyclacene Framework by Repetitive Diels–Alder Cycloadditions
Abstract
:1. Introduction
2. Results and Discussion
2.1. Computations
2.2. Synthesis
2.3. Properties of Macrocycle 12
3. Materials and Methods
3.1. General Methods
3.2. Synthetic Procedures
3.3. X-ray Crystallographic Data
3.4. Computational Chemistry
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Sample Availability
References
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No. | 11a | 12 | ||
---|---|---|---|---|
δC | δH | δC | δH | |
1 | 101.2, CH2 | Ha: 4.70, Hb: 4.86 | 31.16a, CH2 or 31.19a, CH2 | Ha/Hb: 2.57–2.48/2.20–2.04 |
2 | 144.4, C | - | 147.5, C or 147.4, C | - |
3 | 53.6, CH | 3.88–3.86 | 57.0, CH | 4.14–4.12 |
4 | 133.8, CH | 6.39–6.37 | 139.8, CH | 6.75–6.73 |
5 | 137.5, C | - | 147.5, C or 147.4, C | - |
6 | 30.7, CH2 | Ha/Hb: 2.60–2.55/2.18–2.12 | 31.16a, CH2 or 31.19a, CH2 | Ha/Hb: 2.57–2.48/2.20–2.04 |
7 | 43.1, CH | 1.36–1.31 or 1.31–1.25 or 1.25–1.20 | 46.3, CH or 45.8, CH | 1.36–1.31 or 1.31–1.25 or 1.25–1.20 |
8 | 85.19 a, CH or 85.24 a, CH | 4.87 | 84.3, CH or 84.0, CH | 4.79 |
9 | 144.8, C or 144.7, C | - | 145.2, C or 145.1, C | - |
10 | 110.2, CH | 6.95 | 110.0, CH | 6.85 |
11 | 144.8, C or 144.7, C | - | 145.2, C or 145.1, C | - |
12 | 85.19 a, CH or 85.24 a, CH | 4.85 | 84.3, CH or 84.0, CH | 4.82 |
13 | 42.9, CH | 1.77–1.71 | 47.2, CH | 1.36–1.31 or 1.31–1.25 or 1.25–1.20 |
14 | 31.4, CH2 | Ha/Hb: 2.70–2.65/2.12–2.06 | 31.7, CH2 | Ha/Hb: 2.57–2.48/2.23–2.17 |
15 | 143.8, C | - | 147.8, C | - |
16 | 55.3, CH | 4.15–4.13 | 56.3, CH | 4.23–4.21 |
17 | 139.5, CH | 6.77–6.75 | 139.0, CH | 6.82–6.80 |
18 | 140.8, C | - | 143.3, C | - |
19 | 33.7, CH2 | Ha, Hb: 3.49–3.33 | 34.3, CH2 | Ha/Hb: 3.53–3.46/3.26–3.19 |
20 | 130.7, C | - | 133.5, C | - |
21 | 120.9, CH | 6.93 | 118.8, CH | 6.77 |
22 | 146.6, C | - | 143.7, C | - |
23 | 82.2, CH | 5.61 | 84.1, CH | 4.81 |
24 | 143.0, CH | 6.91 | 46.3, CH or 45.8, CH | 1.36–1.31 or 1.31–1.25 or 1.25–1.20 |
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Bauer, J.B.; Diab, F.; Maichle-Mössmer, C.; Schubert, H.; Bettinger, H.F. Synthesis of the [11]Cyclacene Framework by Repetitive Diels–Alder Cycloadditions. Molecules 2021, 26, 3047. https://doi.org/10.3390/molecules26103047
Bauer JB, Diab F, Maichle-Mössmer C, Schubert H, Bettinger HF. Synthesis of the [11]Cyclacene Framework by Repetitive Diels–Alder Cycloadditions. Molecules. 2021; 26(10):3047. https://doi.org/10.3390/molecules26103047
Chicago/Turabian StyleBauer, John B., Fatima Diab, Cäcilia Maichle-Mössmer, Hartmut Schubert, and Holger F. Bettinger. 2021. "Synthesis of the [11]Cyclacene Framework by Repetitive Diels–Alder Cycloadditions" Molecules 26, no. 10: 3047. https://doi.org/10.3390/molecules26103047