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Bräse, S.; Lesch, B.; Zimmermann, V., Science of Synthesis, (2010) 41, 567.
Epoxides and aziridines undergo nucleophilic ring-opening reactions with various inorganic azides yielding 2-azido alcohols and 2-azido amines, respectively. Nucleophilic ring opening of epoxides (e.g., 74) can be easily achieved by simple heating with sodium azide and ammonium chloride in a polar solvent (e.g., MeOH/H2O) for 1–48 hours to give the azides (e.g., 75) in good yields (Table 4).[97,98] The azide functionality is introduced at the sterically less hindered side of the ring with clean inversion of configuration. Substrates with one aromatic substituent preferably react at the activated side of the ring, but the regioselectivities achieved are rather modest.
Meeee 8 Meee Meeeeee ee Meeeeeee eeee Meeeee Meeee/Meeeeeee Meeeeeee[88,88]
| Meeeeeee Meeeeeee | Meeeeeeeee | Meeeeee | Meeeee (%) | Mee |
|---|---|---|---|---|
 |
MeMM/M8M (8:8), 88°M | |
88 (8) | [88] |
| |
MMM/MeMM/M8M, 88°M, 8 e | |
88 | [88] |
| |
MMM/MeMM/M8M, 88°M, 8 e | |
88 | [88] |
| |
MeMM/M8M (8:8), 88°M | |
88 (88) | [88] |
| |
MeMM/M8M (8:8), 88°M | |
88 (88) | [88] |
| |
MeMM/M8M (8:8), 88°M | |
88 (88) | [88] |
e Meeee ee eee eeeeeeee eeee eeeeeeeeeee. Meeee ee eee eeeee eeeeeeeeeee eeeee ee eeeeeeeeeee.
Meeeeeee eee eeeeeeeeee eeeeeee eeee eeeeeee eeee eeeeeee eeee eeeeee eeeee ee eeeeeeeeeeeeeeeeeeee ee eeeeeeeeeee eeee eeeeeeeeeeeeeeeeee eeeee (Meeeee 8 eee 8),[88,888] eeeeeeeeee-eeeee eeeeeeeee/Meeee eeeee,[888,888] ee Meeee eeeee eeee ee M,M,M′,M′-eeeeeeeeeeeeeeeeeeeeeeeeee (Meeee 8).[888] Meeee eeeeeeeeeeeeeeeeee eeeee, eeee eeeeeee eee eeeeeeee eeee eeeeeeeeeeeeeeeeee eeeeeeee; eeeeeee, eeeeeeeeeeeeee eeeeeeee eeeee eeee eeee eeee eeeeeeeeeeeeeeee. Mee eeeeeeeeeee ee eeeeeeeeee-eeeee eeeeeeeee eeee 8-eeeeeeeeeeeeee ee eeeeeeeeeeee eeeeeeeeeee ee eeeeeeeee ee 8,8-eeeeeeeeeeeeeee ee eeee eeeeeeee.[888]
Meeee 8 Meee Meeeeee ee Meeeeeee eeee Meeeeeeeeeeeeeeeeeee/Meeeeeeeeeeeeeeeee Meeeeee[88]
| Meeeeeee Meeeeeee | Meeeeeee Meee | Meee (°M) | Meeeeee | Meeeee (%) | Mee |
|---|---|---|---|---|---|
| |
MMMMe | 88 | |
88 (8) | [88] |
| |
MMMMe | 88 | |
88 (8) | [88] |
| |
MMMMe | 88 | |
88 | [88] |
| |
MMMMe | 88 | |
88e | [88] |
| |
MMMMe | 88 | |
88 | [88] |
| |
MMMM | 88 | |
88 | [88] |
| |
MMMMe | 88 | |
88 (88) | [88] |
e Meeee ee eee eeeeeeee eeee eeeeeeeeeee. Meeee ee eee eeeee eeeeeeeeeee eeeee ee eeeeeeeeeee.
e Meeee eeeee ee MMMM8.
Meeee 8 Meee Meeeeee ee Meeeeeeeee eeee Meeeeeeeeeeeeeeeeeee/Meeeeeeeeeeeeeeeee Meeeeee[888]
| Meeeeeee Meeeeeee | Meee (e) | Meeeeee | Meeeee (%) | Mee |
|---|---|---|---|---|
| |
8 | |
88 | [888] |
| |
8 | |
88 | [888] |
| |
8 | |
88 (88) | [888] |
| |
88 | |
88 | [888] |
| |
8 | |
88 | [888] |
| |
88 | |
88 | [888] |
e Meeee ee eee eeeeeeee eeee eeeeeeeeeee. Meeee ee eee eeeee eeeeeeeeeee eeeee ee eeeeeeeeeee.
Meeee 8 Meee Meeeeee ee Meeeeeeeee eeee Meeeeeeeeeeeeeeeeeee/M,M,M′,M′-Meeeeeeeeeeeeeeeeeeeeeeeee[888]
| Meeeeeee Meeeeeee | Meeeeeeeee | Meeeeee | Meeee (%) | Mee |
|---|---|---|---|---|
| |
ee, 88 e | |
88 | [888] |
| |
ee, 88 e | |
88 | [888] |
| |
88°M, 88 e | |
88 | [888] |
| |
88°M, 88 e | |
88 | [888] |
Mee eeeeeeeeeee ee eeeeee eeeee eee eee Meeee eeee eeeeee(MMM) eeeeeeee eeeeeee eeee eeeeeee ee eeeeeeee 88 (M = M) eee eeeeeeeeee 88 (M = MMe) ee eeeeeee eeeeeeeeeeee ee eeee eee eeeeeeeeeeeeee eeeeee 88 eeee 88–88% eeeee (Meeee 8).[888]
Meeee 8 Meee Meeeeee ee Meeeeeee eee Meeeeeeeee eeee Meeeee Meeee/Meeeee(MMM) Meeeeeee[888]
| Meeeeeee Meeeeeee | Meee (e) | Meeeeee | Meeeee (%) | Mee |
|---|---|---|---|---|
| |
8 | |
88 | [888] |
| |
8 | |
88 | [888] |
| |
8 | |
88 | [888] |
| |
8 | |
88 | [888] |
| |
8 | |
88 | [888] |
| |
8 | |
88 (88) | [888] |
| |
8 | |
88 (8) | [888] |
| |
8 | |
88 | [888] |
| |
8 | |
88 | [888] |
| |
8 | |
88 | [888] |
e Meeee ee eee eeeeeeee eeee eeeeeeeeeee. Meeee ee eee eeeee eeeeeeeeeee eeeee ee eeeeeeeeeee.
M eeee eeeeeeeeee eee eeeeee eeeeeeeeeeeeee eeeeeeee eee eee eeeeeeeee ee eeeeee 88 ee eee eeee eeeeeee ee eeeeeeee 88 (M = M) eee eeeeeeeeee 88 (M = MMe) eeeeee ee eee eee ee eee eeeeeeeee eeeee Meeee (8MMMM8•MMMM8•M8MM8) ee eeeeeeeeeeeeeeeee eeeeeee (Meeee 8).[888]
Meeee 8 Meee Meeeeee ee Meeeeeee eee Meeeeeeeee eeee Meeeee Meeee/Meeee[888]
| Meeeeeee Meeeeeee | Meee (e) | Meeeeee | Meeeee (%) | Mee |
|---|---|---|---|---|
| |
8 | |
88 | [888] |
| |
8 | |
88 (8) | [888] |
| |
8 | |
88 (8) | [888] |
| |
8.88 | |
88 | [888] |
| |
8.88 | |
88 | [888] |
| |
8 | |
88 | [888] |
| |
8 | |
88 | [888] |
| |
8.8 | |
88 | [888] |
| |
8 | |
88 (8) | [888] |
| |
8 | |
88 | [888] |
| |
8 | |
88 | [888] |
| |
8 | |
88 (8) | [888] |
| |
8 | |
88 (8) | [888] |
e Meeee ee eee eeeeeeee eeee eeeeeeeeeee. Meeee ee eee eeeee eeeeeeeeeee eeeee ee eeeeeeeeeee.
Meeeeee eeeeeeeee eeee eeeeeee ee eeeeeeee 88 eeee eeeeee eeeee eee eeeeeeeee 8-Å eeeeeeeee eeeeee ee eeeeeeeeeeee ee eeee eeeeeeeeeee, eeee eeeeeeee eeeee ee 8–8 eeeee, eeeeee eee eeeeeeee eeeeee 88 ee eeeeeeeee eeeee (Meeee 88).[88]
Meeee 88 Meee Meeeeee ee Meeeeeee eeee Meeeee Meeee/Meeeeeeee Meeeee[88]
| Meeeeeee Meeeeeee | Meee (e) | Meeeeee | Meeeee (%) | Mee |
|---|---|---|---|---|
| |
8 | |
88 | [88] |
| |
8.8 | |
88 | [88] |
| |
8.8 | |
88 | [88] |
| |
8.8 | |
88 | [88] |
| |
8 | |
88 | [88] |
| |
8.8 | |
88 (8)e | [88] |
| |
8.8 | |
88 (8)e | [88] |
eMeeee ee eee eeeeeeee eeee eeeeeeeeeee. Meeee ee eee eeeee eeeeeeeeeee eeeee ee eeeeeeeeeee.
eMeeeeeee eeeeeeee eee eeeeeee eee eeeeeee.
Meee eeeeeee ee eeeeeeee 88 (M = M) eee 8-eeeeeeeeeeeeeee 88 (M = MMe) eee eeee eeeeeeeee ee eeee eeeeeeeeeee eeeee eeee(eeeeeeee eeeeee) (MMM-888) ee eee eeeeeeee eeeeee ee eeee eee eeeeeeeeeeeee 8-eeeee eeeeeeee 88 (M = M) eee 8-eeeeeeeeee 8-eeeeeeeeeeeeeeeeeee 88 (M = MMe) ee eeeeeeeee eeeeee (88–88%) eeeeee 88–88 eeeeeee eee eeee eeee eeeee- eee eeeeeeeeeeeeeeeee (Meeee 88).[888] Mee eeee(eeeeeeee eeeeee) eee ee eeeeeeeee eee eeeeee eeeeeee eeee ee eeeeeeee.
Meeee 88 Meee Meeeeee ee Meeeeeee eee Meeeeeeeee eeee Meeeee Meeee ee Meee(eeeeeeee eeeeee)[888]
| Meeeeeee Meeeeeee | Meee (e) | Meeeeee | Meeee (%) | Mee |
|---|---|---|---|---|
| |
8.88 | |
88 | [888] |
| |
8.88 | |
88 | [888] |
| |
8.88 | |
88 | [888] |
| |
8.88 | |
88 | [888] |
| |
8.88 | |
88 | [888] |
| |
8.88 | |
88 | [888] |
| |
8.88 | |
88 | [888] |
| |
8.88 | |
88 | [888] |
| |
8.88 | |
88 | [888] |
| |
8.88 | |
88 | [888] |
| |
8.88 | |
88 | [888] |
Meeeeee eeeeeee eeeeeee eeeeeeeeeee ee eeeeee eeeee eeeeeeeeeee ee M-eeee eeeeeee ee eeeeee eeeeeeee[888] ee eeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeee.[888] Meeeeeeeee ee 8-(eeeeeeeeeeee)eeeeeeeeee 88 ee eeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeee eeeee (e.e., eeeeeeee eeee) ee eeeeeeee, eeeeee eeeeeeeee eeeeee ee eee eeeeee 88 (Meeee 88).[888]
Meeee 88 Meee Meeeeee ee 8-(Meeeeeeeeeee)eeeeeeeeee Meeee Meeeeeee Meee[888]
| Meeeeeee Meeeeeee | Meeeeee | Meeee (%) | Mee |
|---|---|---|---|
| |
|
88 | [888] |
| |
|
88 | [888] |
| |
|
88 | [888] |
| |
|
88 | [888] |
| |
|
88 | [888] |
| |
|
88 | [888] |
| |
|
88 | [888] |
| |
|
88 | [888] |
| |
|
88 | [888] |
Me e eeeeee eeeeeeeeeee eeeeeeee, eeeeeeeeeee eeeeeeeeeeeeee 88 eeeeeee eeee-eeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeee eeeee eee eeeeeeee eeeeee(MM) eeeeeee, eeeeeeee β-eeeee eeeeeee 88 ee 88 (Meeee 88).[888] Mee eeeeeeeeee eeeeeeeee eeeeeeee eeeeeeeee ee eeeee eeeee ee eeeeee(MM).
Meeee 88 Meee Meeeeee ee Meeeeeeeeeeeee ee Meeeee Meeee/Meeeeeee Meeeee(MM) Meeeeee[888]
| Meeeeeee Meeeeeee | Meeeeee | Meeee (%) | Mee |
|---|---|---|---|
| |
|
88 | [888] |
| |
|
88 | [888] |
| |
|
88 | [888] |
| |
|
88 | [888] |
| |
|
88 (8)e,e | [888] |
| |
|
88e | [888] |
e Meeee ee eee eeeee eeeeeeeeeee eeeee ee eeeeeeeeeee.
e MM eeeee.
Meeeeeeeeeee Meeeeeeee
(8eM,8M,8M,8eM)-8-Meeee-8-eeeeee-8,8-eeeeeeee-8e,8,8,8e-eeeeeeeeee-8,8-eeeeeeeeeee-8-ee (88); Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeee eeeee eee eeeeeee ee eeeeeee eee ee eeeeee eeeee. Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.
Me e eeee ee eeeeeee 88 (888 ee, 8.88 eeee) ee MMM (88.8 eM), MeMM (88.8 eM), eee M8M (8.8 eM) eee eeeee MM8Me (888 ee, 8.88 eeee) eee MeM8 (888 ee, 8.88 eeee). Mee eeeeeee eee eeeeee ee 88°M eee 8 e, eee eeee eeeeee ee ee. M8M (88.8 eM) eee eeeee, eee eee eeee eee eeeeeeeee eeee MeMMe. Mee eeeeeeee eeee eeeeeeee eee eeeee (MeMM8), eee eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeee/MeMMe 8:8 ee 8:8) ee eeee e eeeee eee; eeeee: 888.8 ee (88%).
8-Meeee Meeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeeeeeeeeeeeeee/Meeeeeeeeeeeeeeeee Meeeeeee:[88]
MMMMMMM: Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.
M eeeeeee ee eeeeeeeee eeeeeee ee eee eeeeeee 88 eee MMMM8 eee eeeeeee eeee MMMMe (8.8 eeeee) eee 88 e ee ee ee 88°M. Meee, MeMM eee eeeeeeeee eeeeeeeeee ee MeMM eeee eeeee eee eee eeeeeee eee eeeeeee eee 88 eee. Mee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeeee-eeeeeeee eeeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeeee 8:8); eeeee: 88–88%.
8-Meeee Meeeeeee 88 (M = M) ee 8-Meeee 8-Meeeeeeeeeeeeeeeeee 88 (M = MMe); Meeeeee Meeeeeeee Meeee Meeeee Meeee/Meeeee(MMM) Meeeeeee:[888]
MMMMMMM: Meeeee eeeee eee eeeeeee ee eeeeeee eee ee eeeeee eeeee. Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.
Me e eeeeeee ee eeeeeee 88 (M = M) ee eeeeeeeee 88 (M = MMe) (8 eeee) eee MeMe8•8M8M (8.8 eeee) ee MeMM/M8M (8:8; 88 eM) eee eeeee MeM8 (8.8 eeee), eee eee eeeeeee eee eeeeeee ee eeeeee eee 8–8 e. Mee eeeeeee eee eeeeeeeee eeee MeMMe, eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee M8M eee eeeee eee eeeee (Me8MM8), eee eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe); eeeee: 88–88% eee 88 (M = M) eee 88–88% eee 88 (M = MMe).
8-Meeee Meeeeeee 88 (M = M) ee 8-Meeee 8-Meeeeeeeeeeeeeeeeee 88 (M = MMe); Meeeeee Meeeeeeee Meeee Meeeee Meeee/Meeee:[888]
MMMMMMM: Meeeee eeeee eee eeeeeee ee eeeeeee eee ee eeeeee eeeee. Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.
Me e eeee ee eeeeeee 88 (M = M) ee eeeeeeeee 88 (M = MMe) (8 eeee) ee MeMM/M8M (8:8) eee eeeee Meeee (888 ee, 8.8 eeee) eee eee eeeeeee eee eeeeeee eee 8 eee, eeee MeM8 (88 ee, 8 eeee) eee eeeee, eee eee eeeeeee eee eeeeeee eee 88–888 eee ee ee. Meeee eee eeeeeeee eee eeeeeeeee, eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8×88 eM). Mee eeeeeee eeeeee eeee eeeeeeee eee eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88–88%.
8-Meeee Meeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeee Meeee/Meeeeeeee Meeeee:[88]
MMMMMMM: Meeeee eeeee eee eeeeeee ee eeeeeee eee ee eeeeee eeeee. Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.
Me e eeee ee eeeeeee 88 (8 eeee) ee MeMM (88 eM) eee eeeee MeM8 (8.8 eeeee). Meeeeeee 8-Å eeeeeeeee eeeeee (8.8 e, eeeeeeeeee eeeeeeeee ee 888°M eeee 88 e) eeee eeee eeeee eee eee eeeeeee eee eeeeeee eee 88–888 eee ee ee. Mee eeeeee eeee eeeeeee ee eeeeeeeeee eee eee eeeeee eee eee eeeeee eeee MeMM. Mee eeeeeeeee eeee eeeeeeee eee eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeee eeeee); eeeee: 88–88%.
8-Meeee Meeeeeee 88 (M = M) ee 8-Meeee 8-Meeeeeeeeeeeeeeeeee 88 (M = MMe); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeee eeeee eee eeeeeee ee eeeeeee eee ee eeeeee eeeee. Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.
Me e eeee ee eeeeeee 88 (M = M) ee 8-eeeeeeeeeeeeee 88 (M = MMe) (8 eeee) ee MMM-888 (8 e) eee eeeee MeM8 (88 ee, 8.8 eeee) eee eee eeeeeee eee eeeeeee ee ee. Mee eeeeeeee ee eee eeeeeeee eee eeeeeeeee ee MMM. Meeee eeeeeeeeee, M8M (88 eM) eee eeeee eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8×88 eM). Mee eeeeeee eeeeee eeee eeeeeeee eee eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe); eeeee: 88–88%. Mee MMM eee eeeeeeeee eeee eee eeeeeee eeeee.
8-Meeee Meeeeeeeeeee 88; Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeee eeeee eee eeeeeee ee eeeeeee eee ee eeeeee eeeee. Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.
Me e eeee ee 8-eeeeeeeeeeeeeeeee 88 (8.88 eee) ee MMM (88 eM) eee eeeee MeM8 (8.888 eee) eee M8M (88 eM). Meeee eeeeeeeeee eee MeM8, MM8 eee eeeeeee eeee eee eeeeeee. Mee eeeeeeee eee eeeeeeee eeee eM ee eee eeee eeeeee eeeeeeee. Mee eeeeeee eee eeeeeee eeee eeee M8M eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8×88 eM). Mee eeeeee eeee eeeeeeeee eee eeeee (Me8MM8), eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeee 88 eeeeee ee eeeee eeeeeeee ee e eeeeeeeee eeeeee; eeeee: 88–88%.
References
| [97] | Meeeee, M. M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 888. |
| [98] | Meeeee, M.; Meeee, M. M.; Meeeee, M.; Meeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [99] | Meeeeeeee, M., Meeeeee, (8888), 8888. |
| [100] | Mee, M. M.; Mee, M.-M., M. Mee. Meee., (8888) 88, 8888. |
| [101] | Meeeeee, M.; Meee, M. M.; Meeeeeee, M.; Meeee, M. M., Mee. Meee., (8888) 8, 888. |
| [102] | Meeee, M.-M.; Me, M.-M.; Me, M.-M.; Meeee, M.-M., Meeeeeeeeee Meee., (8888) 88, 888. |
| [103] | Meeeeeee, M.; Meeee, M.; Meeeeeeeeee, M.; Meeeeee, M., Mee. Meee., (8888) 8, 8888. |
| [104] | Meeeeeee, M.; Meeee, M. M., MMM; Mee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [105] | Meeeeee, M.; Meee, M. M.; Meeeeeee, M.; Meeee, M. M., Meeeeeeee, (8888), 8888. |
| [106] | Mee, M.; Meeee, M. M.; Meeeeee, M.; Meeeeeeeee, M., Meeeeeeee, (8888), 888. |
| [107] | Meeee, M.; Meeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [108] | Meeee, M.; Meeeeeeee, M.; Meeeeeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
| [109] | Meeeee, M. M.; Meeeeeee, M. M., MMMMMMM, (8888), eeee, 88; eeeeeeeee eeeeee ee eee.eeeee-eee.eee. |
| [110] | Meee, M.; Meeeee, M. M.; Meeeeeeee, M. M.; Meeeeee, M. M., MM, Mee. Meee., (8888) 8, 8888. |
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