Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction †
Abstract
:1. Introduction
2. Materials and Methods
2.1. Synthesis of 5,5-Dimethyl-2-thioxo-2-vinylsulfanyl-[1,3,2]dioxaphosphorinane
2.2. A Typical Procedure for the Preparation of Vinyl Disulfides 2 from S-vinyl Thiotosylate and Representative Analytical Data
2.3. A Typical Procedure for the Preparation of benzo[b][1,4]thiazine disulfanyl derivatives 7 and Representative Analytical Data
3. Results and Discussion
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 1 | R | Yield (%) 2 | Yield (%) 2 |
---|---|---|---|
1 | –n–C12H25 1a | 93 2a | - |
2 | –(CH2)9CH=CH2 1b | 82 2b | - |
3 | –(CH2)10COOMe 1c | 73 2c | - |
4 | –(CH2)11OMe 1d | 62 2d | - |
5 | –(CH2)11SAc 1e | 85 2e | - |
6 | –(CH2)2NHBoc 1f | 75 2f | - |
7 | –(CH2)2C6H4–4–CH3 1g | 76 2g | - |
8 | –(CH2)2–3–indyl 1h | 75 2h | - |
9 | –(CH2)2C6H4–4–CF3 1i | 65 2i | - |
10 | –(CH2)2C6H4–4–F 1j | - | 100 3j |
11 | –C6H4–4–CH3 1k | - | 100 3k |
12 | –CH2–2–naphthyl 1l | - | 80 3l |
13 | –CH2C6H4–4–NO2 1m | - | 70 3m |
14 | –CH2C6H4–4–OMe 1n | - | 85 3n |
15 | –CH2C6H4–4–CN 1o | - | 75 3o |
16 | –(CH2)2C6H4–4–OMe 1p | - | 86 3p |
17 | –CH2Ph 1r | - | 76 3r |
Entry 1 | R 1 | Yield (%) 2 |
---|---|---|
1 | –n–C12H25 4a | 97 2a |
2 | –(CH2)10COOMe 4c | 88 2c |
3 | –(CH2)2C6H4–4–F 4j | 90 2j |
4 | –C6H4–4–CH3 4k | 96 2k |
5 | –CH2–2–naphthyl 4l | 92 2l |
6 | –CH2C6H4–4–NO2 4m | 80 2m |
7 | –CH2C6H4–4–OMe 4n | 87 2n |
8 | –CH2C6H4–4–CN 4o | 89 2o |
9 | –CH2Ph 4r | 98 2r |
10 | –(CH2)10COOH 4s | 84 2s |
11 | –(CH2)11OH 4t | 91 2t |
Entry 1 | R | Yield (%) 2 | Recovered 2 (%) 2 |
---|---|---|---|
1 | –n–C12H25 2a | 50 7a | 35 2a |
2 | –(CH2)10COOMe 2c | 30 7c | 42 2c |
3 | –CH2C6H4–4–NO2 2m | 29 7m | 46 2m |
4 | –CH2C6H4–4–OMe 2n | 27 7n | 44 2n |
5 | –CH2Ph 2r | 25 7r | 52 2r |
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Jędrzejewski, B.; Musiejuk, M.; Doroszuk, J.; Witt, D. Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction. Materials 2021, 14, 1342. https://doi.org/10.3390/ma14061342
Jędrzejewski B, Musiejuk M, Doroszuk J, Witt D. Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction. Materials. 2021; 14(6):1342. https://doi.org/10.3390/ma14061342
Chicago/Turabian StyleJędrzejewski, Bartosz, Mateusz Musiejuk, Justyna Doroszuk, and Dariusz Witt. 2021. "Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction" Materials 14, no. 6: 1342. https://doi.org/10.3390/ma14061342