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Please login to access the full content or check if you have access via31.25.1.1.1.6 Method 6: Coupling of Diazonium Salts with Elimination of Nitrogen
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Rück-Braun, K.; Dietrich, S.; Kempa, S.; Priewisch, B., Science of Synthesis, (2007) 31, 1451.
In the Sandmeyer reaction, aryl radicals are formed from arenediazonium ions by reduction with copper(I) salts with release of nitrogen. Symmetrically substituted diazenes 99 are formed in fair to good yields by rapidly mixing solutions of the diazonium salts with freshly prepared tetraamminecopper(I) solutions (Scheme 40).[178,179]
Meeeee 88 Meeeeeeee ee Meeeeeeeeeeee Meeeeeeeeee Meeeeeee[888,888]
M8 | M8 | M8 | Meeeee (%) | Mee |
---|---|---|---|---|
M | M | M | 88 | [888] |
M | M | Me | 88 | [888] |
M | Me | M | 88 | [888] |
M | M | MMe | 88 | [888] |
Me | M | M | 88 | [888] |
MM | M | M | 88 | [888] |
MM8 | M | M | 88 | [888] |
M(MM8)8Me | M | M | 88 | [888] |
e Mee eeeeeeeeee, eee eeeeeeeeeeee eeeeeeeee.
Meeeeeeee eeee eeeeeeeeeee-8- eee -8-eeeeeeeee eeeee eeee eee eeeeeeeeee eeeeeeee ee 88% eee 88% eeeeee.[888] Meeeeeee eee eeee eeeeeeee ee eeeeeee eeeeeeeee eeee eee Meeeeeeee eeeeeeee.[888]
Meeeeeeeeeee Meeeeeeee
8,8-Me-8-eeeeeeeeeeee (88, M8 = M8 = M; M8 = Me); Meeeeee Meeeeeeee:[888]
M eeee ee MeMM8•8M8M (88.8 e, 8.88 eee) ee eee M8M eee eeeeeee eeee 88% MM8MM eeee (88 eM), eeeeeeee ee MM8MM•MMe (8.8 e, 8.88 eee) ee M8M (88 eM). e-Meeeeeeee (88.8 e, 8.88 eee) ee 8 M MMe (888 eM) eee eeeeeeeeee ee 8°M eeee MeMM8 (8.8 e, 8.88 eee), eeeeeee ee 8 M eeee eee eeeee, eeeeeeee, eee eeeeeee (8 eee) eeeee ee eee Me(M) eeee. Meeeeeeee ee Me8M eeeeeee eeeeeee. Meeee 8 e, eee eeeeeee eee eeeeeeee eee eee eeeeeee eee eeeeee eeee eee MMe, M8M, eee MeMM, eee eeeee eeee M8M. Meeeeeeeeeeeeeeee (MeMM) eeee eee eeee eeeeeee; eeeee: 88.8 e (88%); ee 88–88°M.
References
[178] | Meeeeeeeeeee, M. M., Me. Meeeee. Meee., (8888) 88, 888; Meee. Meeee., (8888) 88, 888. |
[179] | Meeeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[180] | Meeeee, M.; Meeee, M. M.; Meeeeee, M. M.; Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
- 8.Meeeee-Meee, (8888) M 88e8, 88.