The First Example of the Friedel–Crafts Cyclization Leading to (10-Hydroxy-9,10-dihydroanthr-9-yl)phosphonium Salts without the Expected Bradsher Dehydration
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Procedure for Synthesis of o-Acetalaryl(aryl)methanols
3.2. General Procedures for Synthesis of (10-hydroxy-9,10-dihydroanthr-9-yl)phosphonium Salts
3.2.1. Synthesis of Phosphonium Salts 12A and 13A
3.2.2. Synthesis of Phosphonium Salts 11A and 14A–16A
3.2.3. General Procedure for Replacing Chloride Anion with PF6− or BPh4−: Synthesis of Phosphonium Salts trans-13PF6 and 14BPh4
3.3. Synthesis of Phosphonium Salt 18I
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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Compound 2 | 1H NMR | 13C{1H} NMR | Isomer Ratio 4 | |||||
---|---|---|---|---|---|---|---|---|
δPCH (ppm) | 2JPH (Hz) | δCHOH (ppm) | 5JPH (Hz) | δPCH (ppm) | 1JPC (Hz) | δCHOH(4JCP) (ppm) | trans:cis (Isolated Yield%) | |
- 3 | - | 5.15 | 7.5 | 81.6 | 57.0 | 88.7 | 3.6:1 (79) | |
7.40 | 8.0 | 6.36 | 11.3 | 79.9 | 56.0 | 88.4 | ||
7.47 | 11.0 | 5.03 | 7.4 | 81.9 | 58.2 | 88.6 | 3.9:1 (54) | |
8.15 | 10.1 | 5.49 | 6.7 | 80.1 | 57.1 | 87.6 | 5:1 (57) | |
8.41 | 10.2 | 5.25 | 7.1 | 81.9 | 55.7 | 88.8 | 12.3:1 (18) | |
6.64 | 7.8 | 5.18 | 7.3 | 81.2 | 57.7 | 88.7 | (83) | |
8.20 | 10.2 | 5.09 | 7.3 | 81.6 | 55.8 | 88.8 | 9:1 (38) | |
7.15 | 9.8 | 5.71 | 7.1 | 80.3 | 59.5 | 88.8 | 1.4:1 (95) | |
- 3 | - | 6.46 | 11.0 | 78.9 | 65.0 | 88.3 (2.7) | ||
8.20 | 10.2 | 5.09 | 7.3 | 81.6 | 55.8 | 88.8 | 1.2:1 (83) | |
7.28 | 8.3 | 6.42 | 11.0 | 78.9 | 64.1 | 88.1 (2.7) | ||
7.74 | 7.6 | 5.59 | 7.2 | 80.4 | 57.9 | 88.4 | 1.3:1 (85) | |
7.44 | 7.5 | 6.27 | 10.7 | 78.7 | 64.0 | 87.9 | ||
7.26 | 8.1 | 5.74 | 7.1 | 80.4 | 59.7 | 88.8 | 1.4:1 (83) | |
7.03 | 9.1 | 6.46 | 11.1 | 79.1 | 64.4 | 88.3 (2.4) | ||
6.59 | 7.4 | 5.78 | 7.3 | 80.3 | 60.9 | 89.0 | 1.5:1 (88) | |
6.39 | 9.6 | 6.4 | 10.9 | 79.0 | 65.6 | 88.5 (2.3) | ||
8.32 | 7.8 | 5.5 | 7.5 | 80.9 | 57.3 | 88.3 | 1.4:1 (82) | |
8.09 | 8.0 | 6.3 | 11.3 | 79.4 | 62.5 | 87.9 (2.8) | ||
7.19 | 9.8 | 5.7 | 7.0 | 80.2 | 59.4 | 88.9 | 3.1:1 (73) | |
6.88 | 8.7 | 6.4 | 7.1 | 78.7 | 64.2 | 88.2 (2.4) | ||
- 3 | - | 5.7 | 7.0 | 80.3 | 60.1 | 88.5 | 1.2:1 (75) | |
- 3 | - | 6.7 | 9.6 | 79.1 | 64.4 | 88.0 (2.0) |
Assignment | Observed Frequencies (cm−1) | Calculated Frequencies (cm−1) | |
---|---|---|---|
14Cl | 14Cl trans-A | 16Cl cis-C | |
υ(O-H) | 3393 | 3376 | 2760 |
υ(C-H)equatorial | 2876 | - | 2916 |
υ(C-H)axial | 2819 | 2859 | - |
δ(O-H) | 1372 | 1386 | 1390 |
δ(O-H) | 1304 | 1329 | 1330 |
υ(C-O)equatorial | 1115 | 1049 | - |
υ(C-O)axial | 1016 | - | 1017 |
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Owsianik, K.; Różycka-Sokołowska, E.; Koprowski, M.; Turek, M.; Knopik, Ł.; Vivek, V.; Dudziński, B.; Bałczewski, P. The First Example of the Friedel–Crafts Cyclization Leading to (10-Hydroxy-9,10-dihydroanthr-9-yl)phosphonium Salts without the Expected Bradsher Dehydration. Int. J. Mol. Sci. 2024, 25, 1741. https://doi.org/10.3390/ijms25031741
Owsianik K, Różycka-Sokołowska E, Koprowski M, Turek M, Knopik Ł, Vivek V, Dudziński B, Bałczewski P. The First Example of the Friedel–Crafts Cyclization Leading to (10-Hydroxy-9,10-dihydroanthr-9-yl)phosphonium Salts without the Expected Bradsher Dehydration. International Journal of Molecular Sciences. 2024; 25(3):1741. https://doi.org/10.3390/ijms25031741
Chicago/Turabian StyleOwsianik, Krzysztof, Ewa Różycka-Sokołowska, Marek Koprowski, Marika Turek, Łucja Knopik, Vivek Vivek, Bogdan Dudziński, and Piotr Bałczewski. 2024. "The First Example of the Friedel–Crafts Cyclization Leading to (10-Hydroxy-9,10-dihydroanthr-9-yl)phosphonium Salts without the Expected Bradsher Dehydration" International Journal of Molecular Sciences 25, no. 3: 1741. https://doi.org/10.3390/ijms25031741