Self-Terminating, Oxidative Radical Cyclizations
Abstract
:Introduction
Results and Discussion
1. Inorganic Radicals
Entry | 9 | X | Yield (%) |
---|---|---|---|
1 | a | NO2[a] | 10a: 53, 11: 17[b] |
2 | b | NO2[a] | 10b: 35[b,c] |
3 | a | SO3− | 10a: 52, 11: 27[d] |
4 | a | H | 10a + 11: 63[d,e] |
5 | a | RC(O); R = Me[f] | 10a: 35, 11: 31[d,e] |
6 | a | RC(O); R = C6H5[f] | 10a: 42,11: 39[d,e] |
7 | a | RC(O); R = 4-MeOC6H4[f] | 10a: 47,11: 42[d,e] |
8 | a | ROC(O); R = Me[f] | 10a + 11: 94[d,e] |
9 | a | ROC(O); R = Me[f] | 10a + 11: 52[d,e] |
10 | a | ROC(O); R = Allyl[f] | 10a + 11: 89[d,e] |
11 | a | ROC(O); R = C6H5[f] | 10a + 11: 72[d,e] |
12 | a | ROC(O)C(O); R = Et[f] | 10a + 11: 82[d,e] |
13 | a | R2NC(O); R = Et[f] | 10a + 11: 89[d,e] |
14 | a | R2NC(O); R = Et[f] | 10a + 11: 69[d,e] |
15 | a | R2NC(O); R = Et, C6H5[f] | 10a + 11: 58[d,e] |
16 | a | R; R = Me[[g] | 10a + 11: 32[d,e] |
17 | a | R2N; R,R = –C(O)CH2CH2C(O)– | 10a + 11: 50[d,e,h] |
18 | a | R2N; R,R = –C(O)-2-C6H4-C(O)– | 10a + 11: 27[d,e,h] |
Entry | 12 | X | Yield(%) (13+14) | Product ratio (%)[a] | ||
---|---|---|---|---|---|---|
13b | 13c | 14 | ||||
1 | a | NO2[b] | 13a: 77[c] | |||
2 | b | NO2[b] | 74[c] | 43 | 57 | − |
3 | b | SO3− | 52[d] | 43 | 43 | 14 |
4 | c | NO2[b] | 13d: 11[c] | |||
5 | b | H | 82[d,e] | 6 | 12 | 82 |
6 | b | RC(O); R = Me[f] | 43[d,e,g] | 5 | 6 | 89 |
7 | b | RC(O); R = C6H5[f] | 57[d,e] | 4 | 8 | 88 |
8 | b | RC(O); R = 4-MeC6H4[f] | 93[d,e] | 5 | 5 | 90 |
9 | b | RC(O); R = 4-MeOC6H4[f] | 80[d,e] | 6 | 9 | 85 |
10 | b | RC(O); R = 3-NO2C6H4[f] | 74[d,e] | 10 | 29 | 61 |
11 | b | RC(O); R = 4-NO2C6H4[f] | 85[d,e] | 11 | 30 | 59 |
12 | b | RC(O); R = 4-FC6H4[f] | 88[d,e] | 7 | 9 | 84 |
13 | b | ROC(O); R = Me[f] | 84[d,e] | 9 | 12 | 79 |
14 | b | ROC(O); R = Allyl[f] | 75[d,e] | 10 | 18 | 72 |
15 | b | ROC(O); R = C6H5[f] | 63[d,e] | 15 | 34 | 51 |
16 | b | ROC(O)C(O); R = Et[f] | 48[d,e,g] | 10 | 17 | 73 |
17 | b | R2NC(O); R = Et[f] | 75[d,e] | 11 | 13 | 76 |
18 | b | R; R = Me[h] | 53[d,e] | 6 | 49 | 45 |
2. Other Oxygen-Centered Radicals
3. Some Mechanistic Considerations
Conclusions and Future Outlook
Acknowledgments
References and Notes
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Dreessen, T.; Jargstorff, C.; Lietzau, L.; Plath, C.; Stademann, A.; Wille, U. Self-Terminating, Oxidative Radical Cyclizations. Molecules 2004, 9, 480-497. https://doi.org/10.3390/90600480
Dreessen T, Jargstorff C, Lietzau L, Plath C, Stademann A, Wille U. Self-Terminating, Oxidative Radical Cyclizations. Molecules. 2004; 9(6):480-497. https://doi.org/10.3390/90600480
Chicago/Turabian StyleDreessen, Tim, Christian Jargstorff, Lars Lietzau, Christian Plath, Arne Stademann, and Uta Wille. 2004. "Self-Terminating, Oxidative Radical Cyclizations" Molecules 9, no. 6: 480-497. https://doi.org/10.3390/90600480