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Please login to access the full content or check if you have access via3.3.6.8 Method 8: Halogenation of Organomercury(II) Derivatives
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Kitching, W.; Glenn, M., Science of Synthesis, (2004) 3, 286.
The halogenation of organomercury(II) derivatives has been studied extensively[667] and effected on an extremely wide variety of examples. Essentially the reaction is widely employed to determine the position of the mercury atom where other methods, such as NMR, are unavailable. Other studies focus on the mechanistic aspects of the reaction, and a comprehensive mechanistic review[667] and a detailed summary of substrates halogenated via organomercury(II) derivatives is available.[710]
Meee e eeeeeeeee eeeee ee eeee, eee eeeeeeee eee eeeeee eeeeeeeeeee, ee eee eeeeeeeee eeeeeeeeeeeee(MM) eeeeeeeeeee eee eeeeeeeee eeeeeeeee eeee eeeeeee ee eeeeeeeee eeee eee eeeeee eeeeeeeeeee. Meeeeee, eeeee eee eeeeeeeeee, eeee ee eee eeeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeee ee eeeee β-eeeeeeeeeee eeeeeee eeeeeee,[888,888] eee eeeeeeeeeeee ee eeeeeeeeeeee(MM) eeeeeeeeeee[888,888] [e.e., ee eee[(M)-8-eeeeeeee-8-eeee]eeeeeee(MM) (888) (Meeeee 888)[888] eee eee-8-eeeeeeeeeee(MM) eeeeeeeeeee, eee Meeeeee 8.8.8.8],[888] eee eee eeeeeeeeeeee ee eeeeeeeeeee eeeeeeeeeee(MM) eeeeeee ee eeeee eeeeeeeeeeeeeeee eee eeeeee eeeeeeeeee ee eeeeee eeeee.[888,888]
Meeeee 888 Meeeeeeeeeee ee Mee[(M)-8-eeeeeeee-8-eeee]eeeeeee(MM) Me Meee 8-Meeee-8-eeeeeeee-8-eee[888]
Mee eeeeeeeee ee eeeeeeeeeeee eeeeeee ee eee eeeeeee, eee eeeeeeeeeeee eeeee, eee eee eeeeeeeeeeeee(MM) eeeeeeeeee, eee eeeeee eeee-eeeeeee ee eeeeeeeeeeeee eeeeeeeee eee ee eeeeeeee.[888] Mee eeeeeee, eeeeeeeeee ee eeeeeeeeeeee(MM) eeeeeee ee eeeeeee ee e eeee-eeeeeee eeeeeee,[888] eeeee eee eeee eeeeeeee eeee eeeeee eeeee ee eeeeeee eeeeeee eeeeeeee e eeeeeeeeeee eeeeeeeeeeeee eeeeeeeeeeee.
Me eeeeeeee, eee eeeeeeeeeeeeee eeeeeee ee eeeeeeeeeeee ee eeeeeeeee ee eee eeeeeeeeee eeee. Meeeeee eeeeeeeeee ee eee- eee eeeee-8-eeeeee eee -8-eeee-eeeeeeeeeeeeeeeeeeeeee(MM) eeeeeee eeeeeee eeee eeeee eeeeeee ee eeeeeeee eeeee ee eeeeeeee eeeeeeeee ee eeeeeeeeeeeee, eeeeeee ee eeeeee eeeeeeeeeeeee eeeeeeeee 88:88 eeeeeeeeeeeeee eeeeeeee.[888] Meeeeee, eeeee ee eee ee eeeeeeee eeee eeee eeeeeeee eeeee eeeeeee eeeeeeeeeeee eeee eeeeeee, eeeee eeeeeeeeee eeeeeee eeeeeeeeeeee eeee eeeeeeee ee eeeeeeeeeeeee.[888,888] Meeeee 888 eeeee eeee eeeeeee eee eee eeeee- eee eee-8-eeeeeeeeeeeeeeee eeeeee 888.[888]
Meeeee 888 Meeeee ee Meeeeee eee Meeeeeeeee ee eee Meeeeeeeeeeeeee ee Meeeeee Meeeeeee ee eee- eee eeeee-8-Meeeeeeeeeeeeeeeeeeeeee(MM) Meeeeeee[888]
Meeeee 888 | Meeeeee | Meeeeeeeee | % Meeeeeeee ee 888 | Mee |
---|---|---|---|---|
eeeee | MMe8 | M8 | 8 | [888] |
eeeee | MM8 | M8 | 8 | [888] |
eee | MMe8 | M8 | 8 | [888] |
eeeee | MeMM | M8 | 88 | [888] |
eee | MeMM | M8 | 88 | [888] |
eeeee | MeMM | eee | 88 | [888] |
eeeee | MeMM | eee | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
8-Meee-8-eeeeeeeeee[8.8.8]eeeeee; Meeeeee Meeeeeeee:[888]
Me e eeee ee 8-(eeeeeeeeeeee)-8-eeeeeeeeee[8.8.8]eeeeee (8.8 e, 88 eeee) ee MMe8 (888 eM) eeeeee ee 8 °M eeeee M8, eee eeeee M8 (8.8 e, 88 eeee). Meeee eee eeeeeee eee eeee eeeeeee eee 8 e ee ee, eee eeeee eeee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeeeeeeeee eeee Me8M8M8, eeeee, eee eeeeeeeeee ee eeeeee eee eeeeeee; eeeee: 8.8 e (88%); ee eeeeeeee eeeeeeeeee eeee ee ee ee ee eeeeeeee.
Meeeeeeeeee-8-eeeeeeeeeee; Meeeeee Meeeeeeee:[888]
Mee(eeeeeeeeeeeeeeeeee)eeeeeee(MM) (888 e, 8 eee) eee M8 (888 e, 8 eee) eeee eeeeee ee e eeee ee 888 °M eee 8 e. Mee eeee eee eeeeeee ee ee eee eeee eee eeeeee. Mee eeeeeee eeeeeee eee eeeeeeee, (eee eee ee e eeeee MM8 eeee eeeeeeeee eee eeee ee eeeee eeeeeee ee eeeeeee) ee eeeee eee eeeee eeeeee (888 e) eeeee ee eeeeeeeeeeee eeee eee eeeeeee; eeeee: 888 e (88%); ee 88 °M.
(M)-8-Meeeeee-8-eeeee-8-eeeeeeeeee-8-eee; Meeeeee Meeeeeeee:[888]
Me 8-eeeeeee-8-eeeeee-8-eeeeeeeeeeeeeeeeee(MM) eeeeeeee (8.88 e, 8 eeee) ee eeeeeeee (88 eM) eee eeeee Me8 (8.88 e, 8 eeee) ee eeeeeeee (88 eM) ee ee eeee 8 eee, eee eee eeeeeeeee eeee eee eeeeeee eee 8 e. Meeee eeeeeeee eeee eee ee MMe ee eeeeee eeeeeeee, eee eeee eee eeeeeeeee eeee eeeeeee. Meeeeeeeeeee eeeeeeee eee eeeeeee; eeeee: 8.8 e (88%); ee 88 °M/Meee.
(M)-8-Meeeeee-8-eeee-8-eeeeeeeeee-8-eee; Meeeeee Meeeeeeee:[888]
Me 8-eeeeeee-8-eeeeee-8-eeeeeeeeeeeeeeeeee(MM) eeeeeeee (8.88 e, 8 eeee) ee MeMM (88 eM) eee eeeee M8 (8.88 e, 8 eeee) ee eeeee eeeeeeee ee ee eeee eeeeeeee. Meeee 8 e, eee eeee eee eeeee ee eee. eeeee (888 eM) eee eeee eeeeeeeee eeee eeeeeee (8 × 88 eM). Mee eeeeeee eee eeeeee eeee ∼8 M ee Me8MM8 eee M8M, eeeee (Me8MM8), eee eeee eeeeeeeeeeee (∼8 eM). Meeeeeeeeeee eeeeeeee eee eeeeeee; eeeee: 8.8 e (88%); ee 888 °M/88 Meee.
eee-8,8-Meeeeeeee-8-eeeeeeeeeeeeeeee; Meeeeee Meeeeeeee:[888]
M eeee ee Me8 (8.88 e, 8 eeee) ee eeeeeeee (8 eM) eee eeeee ee e eeee ee eee-8,8-eeeeeeeeeeeeeeeeeeeeeeeeee(MM) eeeeeee (8.8 e, 8.88 eeee) ee eeeeeeee (8 eM) ee −88 °M eeeee eee M8. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeee eee eeeeee ee ee eee eeeeeee eee 8.8 e. Meeeeeee eee eeeee eeeeeeeee eeee eeeeeee ee eeeee (8 Meee) eee eee eeee eeeeeee eee eeeee ee ee Me8M (888 eM). Mee eeee eee eeeeee eeee eee. ee MeMMM8 eee eeee eee. ee MeMM8, eeeee (MeMM8), eeeeeeee eee eeeeeeeeeeee eeeee eeeeee. Meeeee eeeeeeeeeeeeee (eeeeee eee, 88 e, MMMe8) eeee eee eeeeeee ee e eeeeeee ee eee eee-8-eeeee eee eeeee-8-eeeee eeeeeee; eeeee: 88%.
References
[209] | Meeeeeee, M.; MeMeee, M., M. Meee. Mee., (8888), 8888. |
[257] | Meeeee, M.; Meeeeee, M.; Meeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[302] | Meeee, M. M.; Meeeeeeeee, M. M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
[303] | Meeeeee, M. M.; Meeee, M.; Meeeee, M.; Meeeeeeee, M., Meeeeeeee, (8888), 888. |
[427] | Meee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[446] | Meeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[510] | Meeeee, M. M.; Meee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
[667] | Meeeee, M. M.; Meeeeeee, M., Meeeeeeeeeeee Meeeeeeeeeee ee Meeeeeeeeeeeeeee, MeMeee-Meee: Mee Meee, (8888); ee 88–88. |
[710] | Meeeee, M. M., Me Meeeeeeeeeeee Meeeeeeee ee Meeeeee Meeeeeeee; Meeeeeeeee eee Meeeeeeee Meeeee 88, Meeeee, M.; Meee, M.-M.; Meee, M. M.; Meeeeeee, M. eee M.; Meeee, M. M.; Meeeeeeee, M., Mee.; Meeeeeee: Mee Meee, (8888); ee 888–888. |
[711] | Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[712] | Meeeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[713] | Mee, M. M.; Meeeeeee, M.; Meeeee, M. M., M. Meee. Mee., (8888), 8888. |
[714] | Meeee, M. M.; Meeeee, M. M., M. Meeeeeeee. Meee., (8888) 88, 888. |
[715] | Meeeee, M., Me.M. Meeeeeeeeeee, Meeeeeeeee ee Meeeeeeeee, Mee Meeeeee, (8888). |
[716] | Meeeee, M. M.; Meee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[717] | Meeeeee, M. M.; Meeeee, M. M.; Meee, M. M.; Meeeeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88M/8, 888.
- 8.Meeeee-Meee, (8888) 88/8e, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 88.