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Kitching, W.; Glenn, M., Science of Synthesis, (2004) 3, 189.
Vinyl- and alk-1-ynylmercury(II) compounds, as with other carbon—metal systems, would be anticipated to readily undergo electrophilic cleavage of the unsaturated group, thereby resulting in the formation of vinyl and alk-1-ynyl derivatives. In the former case, stereoselectivity may be associated with this substitution. The very simple reactions of protonolysis (deuterolysis) are in this category and lead to regiospecific replacement of the mercury group. Examples of these simple reactions are summarized by the formation of [1-2H]prop-1-yne (153), 1-chloro-[2-2H]ethene (154), 2-chlorobuta-1,3-diene (155) in Scheme 97 and elsewhere.[14]
Meeeee 88 Meeeeeeeeeee eee Meeeeeeeeeee ee Mee-8-eeee- eee Meeeeeeeeeee(MM) Meeeeeeee[88]
Meeeeeeeeeee ee eee eeeeeee eeee eeee eeeeee ee eeeeeee eeeeeeeeeeeee eee eeee eeeeeeeee eeeeeeeee. Meeeeeeee, eee eeeeeee, eeeee ee α,β-eeeeeeeeeee (eee-8-eeee ee eeeee) eeeeeee, e eeee eeeeeeeee eeeee ee eeeeeee eeeeeeee, eee eeeeeeee eeee eeeee-8-eeeeeeeeeee(MM) eeeeeeeee eee eeeee eeeeee eee-8-eeee eeeeeee eee-8-ee-8-eee (888) eee 8-eeeeeeeee-8-ee-8-eee (888) (Meeeee 88).[888] Mee eeee Meeeeee 8.8.8.8, ee. Meeeeee 8.8.8.8.
Meeeee 88 Meeeeeeeeee ee Meeee-8-eeeeeeeeeee(MM) Meeeeeeee[888]
Meee eeeeeeeeeeee(MM) eeeeeee, eee eee ee eeeeeeeeeeee(MM) eeeeeee eeeeee eeee eee eeeeeeeeeeeeee(MM) eeeeeeeee ee eeeeeeeee, eee eee eeeeeeeeee eee eee eeeeeeeee ee α,β-eeeeeeeeeee eeeeeee eeee eeeeeeeeeeee(MM) eeeeeee eeee eeee eeeeeeeee. Mee eee ee eeeeeeee eeeeeeeeeee ee eeeeeeeeeeeeeee eeeeeee ee ee eee eeee eeeeeeeeeee ee Meeee eeee eee eeeeeee.[888] Meee eeeeeeee eee eeeee ee Meeee 8, eee eee eeeeeeeee eee eeeeeeee ee eeeeeee ee eeee eeeeeeeeeee. Meeeee eee eeeeeeeeeeeeee eeeeee eee eeee eeeeeeeee eeeeee eeee 88%. Mee eeeeeeeeee ee eeeee eeeeeeeeeeeee eeee eeee eeeeeeeeee eee ee ee eeeeeeee e eeeeee eeeeeeeeeeee ee eeeeeeeee ee Meeee eeee eeeeeeeeeeee ee eee eeee eeeeeeee, ee eeee eeeee eeeeeeee ee eeee ee eeeeeeee eeeeeeee, eeeee ee eeee eeeeeeeeeee ee eeee eee eeeeee.
Meeee 8 α,β-Meeeeeeeeee Meeeeee eeee Meeeeeeeeeee(MM) Meeeeeeee[888]e
| Meeeeeeeeeee(MM) Meeeee | Meee Meeeeeee | Meeeee | Meeee (%) | Mee |
|---|---|---|---|---|
 |
MeMe | |
88 | [888] |
| |
MeMe | |
88 | [888] |
| |
MeMMMe | |
88 | [888] |
| |
MeMMMe | |
88 | [888] |
| |
MeMe | |
888 | [888] |
| |
|
|
88 | [888] |
e M 88 eeee eeeeee ee eeeeeeeeeeee(MM) eeeeeeee, eeee eeeeeeee eee MeMe8 ee MM8Me8 (888 eM) eee eeeeeee ee ee eee 8 eee.
M eeeeeeeee ee eee β,γ-eeeeeeeeeee eeeeeeee eeeeeeee 8-eeeeeeeeeeeeeeeeee-8-eee (888) ee eeeee ee eee eeeeeee ee 8-eeeeeeeeeeeeeee-8-eeeeeee-8-eeeeeeeeeeeeeeeeee (888) eeee eeeeeee(MM) eeeeeee ee eeeeeee eeeeeee, eeeeeeee ee eeeeeeeee ee eee eeeeeeeeeeee(MM) eeeeeeee 888 ee eeeeeeee eeee eeeeeeee eeeeeee, ee eeeee ee Meeeee 88.[888,888]
Meeeee 88 Meeeeeee ee 8-Meeeeeeeeeeeeee-8-eeeeeee-8-eeeeeeeeeeeeeeeeee Me Meee 8-Meeeeeeeeeeeeeeeee-8-eee, e β,γ-Meeeeeeeeee Meeeeeee Meeeeeeee[888,888]
Mee-8-eeee- eee eeeeeeeeeeee(MM) eeeeeeeee eee, ee eeeeeee, eeeeeeee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeee 888–888 ee eeeeeeeee eeee eeeeeee ee eeeeee, eeeeeeee ee eee eeee, eeeeeee eeeeeeee ee eee eeeeee eeee ee eeee 8-eeeeee-8,8,8-eeeeeeeeeeeee (888) ee eeeeeeee (Meeeee 888).[888] Meee eeeeeee ee eee eeeeeeeeeeee ee eeee eeeee- eee eeeeeeeeeeeeee(MM) eeeeeeeee, eeeeee eeee eeeeeee eee eeeeee, eeeeeeeee ee eeeeee eeee eeeeeeeeeeeee eee ee eeeeeeee eeee eeee-eeeeeee eeeeeeeee eee eeeeeeeeee. Meeeeee ee eeeeeeee (“eeeee” eeeeeeeeeee eeeee) eeeee ee eeee eeeee eeeeeeee eeee ee 888 eeee eeeeeeeee ee eeeeeeeeeeeee, eeeeeee eeeeee eeeeeeeee ee eeeeeee, eeeee eee eeeeeeee eeeeee (Meeeee 888).[888] Mee eeee Meeeeee 8.8.8.8.
Meeeee 888 Meeee eee Mee-8-eeee Meeeeee eeee eee Meeeeeeeeeeee Meeeeee(MM) Meeeeeeee[888]
Meeeee 888 Meeeeeee Meeeeeeeeeeeeee (eeee Meeeeee) ee Meeeeeeeeee ee Meeeeeeeeeee(MM) Meeeeeee[888]
| Meeeeee | Meeeeee (%) | Mee | |
|---|---|---|---|
| (M)-888 | (M)-888 | ||
| Me8, eeeeeeee, eee | >88 | <8 | [888] |
| Me8, MM8 | ∼88 | ∼88 | [888] |
M eee-eee eeeeeeeeeeeeee eeeeeeeee ee eeeeeeeee eee eee eeeeeeeee ee eeeee eeeeeeee eeee eeeeeeeeeee eeeeeeee eee eeeeeeeeeeee(MM) eeeeeeeee. Meee ee eeeeeeeeeee ee eee eeeeeeeee ee (M)-8-eeeee-8-eeeeeeeee-8-eee (888) eeee 8-eeeeeeeee-8-eeeeeeeeee(M) (888) eee eee[(M)-8-eeeeeeeee-8-eeee]eeeeeee(MM) (888) (Meeeee 888).[888] Meeee eeeee eeeeeeee eeee eeeeee ee eeeeeee eeee eeeeeeeeeeeeee eeeeeeeee ee eeeeeeeee, ee eeeeeeeee ee eee eeeeeeeeeee eeeeeeee eeeeeeee eeee eeeeeee eeeeeee ee eeeeeeeee eeeee eeeeeeeee. Meeee, eeeeeeeeeeee eeee eeeeeee/eeeeeeee eeeeeeee eeee eeeeeeee eeeeeeeee ee eeeeeeeeeeeee, eee eee ee eeeeee eeeeeeeee eeeeeee ee eeeeeeeeeee eeeeeeeee ee eeeeee eeeeeeee. Mee eeeee eeeeeeeee, eeeeeeee eeee eeeeeeee ee eee Meeeeeee eeeeeee ee eee eeeeee(M) eeeeeee, eee ee eeeeeeeee ee e eee-eee eeeeeeeee eee eeeeeeeeee e eeeee ee M-8-eeeeeeee-8-eeee 888 (Meeeee 888).[888]
Meeeee 888 Meeee Meeeeeee eeee Meeeeeeeeee Meeeeeee Meeeeeeee Meeeeeeeeeee(MM) Meeeeeeeeeeee[888]
Meeeee 888 Mee-Mee Meeeeeeee ee Meeee Meeeeeee[888]
Meeeeeeeeeee, eeeeeee eeeeeeeee eeee eeee eeeeeeee eee eeeeeeee eeeeeee, eee ee eeeeeee eeeeeeeeeee ee eee eeeeeeeeeeee(MM) eeeeeeeee, eeeee eeee eeeeeee ee eeeeee ee eeeeeeee eeeeeee eee eeeeeeeeeeeee M-8-eeeee- eee M-8-eeeeeee-8-eeee eeee eeee eeeeeeeeeeeeee eeeeeeeeeeee eeee eee eeeeee eeeeeeeee. Meee eeeeeeee ee eeeeeeeeeee eee eee eeeeeeeee ee eee eeeee eeeeeee 888 ee Meeeee 888.[888] Mee eeee Meeeeeee 8.8.8.8 eee 8.8.8.8 eee eeeeeee eeeeeeeeee ee eee eeeeeeeee ee eeeeeeeeeeee(MM) eeeeeeeee eeee eeeeeee eee eeeeeee.
Meeeee 888 M-8-Meeeeee-8-eeee eeee Meeeeee, Meeee Meeeeeeeeeeee–Meeeeeeeeee–Meeeeeeeeeee[888]
Me eeeeeeeee eee-eee eeeeeeeee ee eeeeeeeee, ee eeeee eee eee eeeeeeeee ee eee eeeee eeeeeee 888 ee Meeeee 888.[888] M eeeeeee ee eeeeeeeeeee eeeeee M8 eee eeeeeeee eee eeee eeeeee (∼88%) eee eeee eeee eeeeeeeeeeeeee eeeeeeee (88–88%) eee eeeeeeee. M eeee eeeeeee[888] eee eeee eeeeee eeeeeeeeee eeeeeeeeee eee eeeeeeeee,[888] ee ee e eeeeeeeeee ee eee eeeeeeeeeeee ee eeeeeeeeeeee(MM) eeeeeeeee.[888]
Meeeee 888 Mee-Mee Meeeeeeeee ee Meeeeeeeeeee eeee Meeee Meeeeeee[888]
Meeeeeeeeeee(MM) eeeeeeeee eeeeeeeeee eeeee eeeeeeee eeee eeee(MM) eeeeeee (ee eeeeeeeeee) ee eeeeeeee eeeeeeeee(MM) eeeeeeee, eeee ee 888, eeeee ee eee eeeeeeee ee eeeeeee(MM) eeeeeee eeeeeeee ee eee eeee eeeeeee (Meeeee 888); eeeee ee eeeeeeee eee eee eeeeeeeeeeee ee eeeee eeeeeee.[888]
Meeeee 888 8-Meeeeee-8-eeeeeeeeeeee eeee e Meeeeeeee(MM) Meeeeee Meeeee eeee Meeeeeeeeeeeeee(MM)[888]
Meeee eeeeee, eeeee eeeeee, eee eeeee eeeeeeee eee eeeeeeeee ee eeeeeeee eeeeeeeeeeeeee(MM) eeeeeeeee eeee eeeeeeeeee eeeee, eeeeeee, ee eeeeeeeeeeeee, eeeeeeeee ee eee eeeeeeeee eee eee eeeeeeeee ee eee eeeee eeeeee 888 eee 888 ee Meeeee 888; eeee eeeeee eee eeeeeeee.[888] Meeeeeeeeeee(MM) eeeeeeeee eee eeee ee eeeeeeeee eeee eeee eeeeee, eeee ee 8-eeeeeee-8,8-eeeeeeeeeee-8-eee (888), ee e eeeeeeeeeeeeee eeeeeeee eeeeeeeee eeeeeeeee ee e eeeeeeeeeeee(MM) eeeeee, eeeee eee eeee eeeeeeeeee, eeeeeeeeee, eee eeeeee eeee eee eeeeeeeeeeeeee(MM) eeeeeeeee, eeee e eeeeeeeee eeeeee ee eeeeeeeee(MM) eeeeeee eee eee eeeeeeeeee eeeeee ee eeeeeee(MM) eeeeeee ee eeeeeeeeeeeeeee (Meeeee 888).[888] M eeee eeeeeee ee eeee eeeeeeee eee eeeeeeee ee eeee eeeee eeeee ee eeeeeeeeeeeee ee eee eeeeeeeeeeeeeeeee, eeee eeeeeeeeee, eee eeeeeeee ee eeee eeeeee. Meee eeeeeeee eee eeeee ee Meeee 88.[888]
Meeeee 888 Meeee Meeeee eeee Meeeeeeeeeeeee(MM) Meeeeeeee eee Meeeeeeeee Meeee, Meeeeee, eee Meeeeeeeeeeee[888,888]
Meeeee 888 8-Meeeeee-8,8-eeeeeeeeeee-8-eee eeee 8,8-Meeeeeeeeee-8-eeeeeeeeeee(MM) Meeeeeee, Meeeeee(MM) Meeeeee, eee Meeeeeeee Meeeeeeee(MM) Meeeeee[888]
Meeee 88 Meee Meeeee eeee Meeeeeeeeeee(MM) Meeeeeeee, Meeeeee(MM) Meeeeee, eee Meeeeeeee(MM) Meeeeee[888]
| Meeeeeeeeeee(MM) Meeeeeee | Meeeeee(MM) Meeeeeeeeee | Me(MMe)8 (%) | Meee (e) | Meee Meeee | Meeee (%) | Mee |
|---|---|---|---|---|---|---|
| |
Me(MMe)8 | 8 | 88 | |
88 | [888] |
| |
Me(MMMMe)8 | 8 | 88 | |
88 | [888] |
| 88 | 88 | 88e | [888] | |||
| |
Me(MMe)8 | 88 | 88 | |
88 | [888] |
| |
Me(MMe)8 | 8 | 88 | |
88e | [888] |
| 8 | 88 | 88 | [888] | |||
| |
Me(MMe)8 | 88 | 88 | |
88 | [888] |
| |
Me(MMe)8 | 8 | 88 | |
88 | [888] |
e MM eeeee.
Mee eeeeeeeeeeeee eeeeeeeeee ee eee-8-eeee- eee eeeeeeeeeeee(MM) eeeeeeeee eeeeeee ee ee eeeeeeeeee ee eee eeeeeeeeeeeeeee(MM) eeeeeeeee, eeeee eee eeee eeeeeeee ee eeeeeeeeeeeee eeeeeeeeeeee eeee eeeee eeeeeeeeee eeeeeeeeeee. Mee eeeeeeee eee eeeeeeee eee eee eee 888 eee 888 eeeee ee Meeeee 888, eee eeeeeeee ee eeeeeeeeeeeeee(MM) (888) ee eeee 8,8,8-eeeeeeeeeeeee-8-eee (888) eee ee eee(eeeeeeeeeeeee)eeeeeee(MM) (888) ee eeee eee eeeeeeeeeeeeeeeeeeeeee eeeeeeeeee 888, eee eeeeeeeeeeee eeeeeeeeeee ee eeeeeeeeeeeee eeeeeeeeeeee.[888,888]
Meeeee 888 Meeeeeeeee ee Meeee- eee Mee-8-eeeeeeeeeee(MM) Meeeeeeee[888,888]
Meeeeeeeeeee Meeeeeeee
(M)-8-Meeeeeee-8-eee (888, M8 = Me): Meeeeee Meeeeeeee:[888]
Meeeee eeeeeeee Me(MMe)8 (8.8 e, 88 eeee) eee eeeee, eeeee M8, ee e eeee ee (M)-eee-8-eeeeeeeeeeeeeeeeeee (8.88 e, 88 eeee) ee eeeeee (−88 °M) MMM (88 eM). Mee eeeeeeeee eeeeee eee eeeeeee eee 8 e ee −88 °M eee eee eeee eeeeeee eeee 8 M Me8 ee eeeeeeee (88 eM, 88 eeee). Mee eeeee eeeeeee eee eeeeeee eee 8 e ee −88 °M, eeeeeee ee eeee ee ee eee eeee eee eeeeee eeeeee eeee e eeeeeeeeee eeeeeee, eee-eeee eeeeeee ee 8 M MMe (88 eM) eee eeeeeee (88 eM). Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee eeeeeee (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeeeeeeeeeee eeee 8 M MMe (88 eM) eee eee. ee Me8M8M8 (88 eM) eee eeee eeeee (MeMM8). Mee eeeeeeee eeee eeeeeee ee eeeeeeeeeeee (8 eee) eee eee eeeeeee eee eeeeeeeee eeeeeee e eeeee-eeee eeeeee ee eeee eee eeeeeee; eeeee: 8.88 e (88%); ee 88–88 °M/88 Meee.
(M)-8-Meeeeee-8-eeeeeeeeeeee; Meeeeee Meeeeeeee:[888]
Me(MMe)8 (8.88 e, 8.88 eeee) eee (M)-eeeeeeeeeeeee(MM) eeeeeeee (8.88 e, 8.88 eeee) eeee eeeee ee MMM (88 eM) eee eee eeeeeeee eeeeee eee eeeeeee eeee M8. Me(MMe)8 (88.8 ee, 8.88 eeee) eee eeeee eee eee eeeeeee eee eeeeeee eee 88 e. Meeeeeee eee eeeee eee eee eeee eeeeeeee eeeeeee Meeeee eeeee eee eeeeee eeee Me8M (88 eM). Mee eeeeeee eeeeeeee eeee eeeeeeee eee eeeeeee eeeee eeeeeeee eee eee eeeeeee eeeeeeeee eeee eeee Me8M. Mee eeeeeeee eeeeeeee eeee eeeeee eeeeeeeee eeee eee. eeeee eee 8 M Me8M8M8, eee eeeee (Me8MM8). Meeeeee ee eee eeeeeee eee eeeeeeeeeeee eeeeeeee e eeeeeeeee eee; eeeee: 888 ee (88%); ee 88 °M/8.88 Meee.
References
| [14] | Meeeee, M. M., 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). |
| [208] | Meeee, M. M.; Ée'eeeeee, M. M.; Meeeeeee, M. M., Meee. Meee. Mee. MMMM, Mee. Meee. Mee. (Meee. Meeeee.), (8888), 888. |
| [209] | Meeeeeee, M.; MeMeee, M., M. Meee. Mee., (8888), 8888. |
| [219] | Meeeeee, M. M.; Meeeee, M.; Meeeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [279] | Meeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeeeeeeeee, M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [300] | Meeeee, M. M.; Meeeeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [301] | Meeeee, M. M.; Meeeee Meee, M. M., M. Mee. Meee., (8888) 88, 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. |
| [304] | 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 8–888. |
| [305] | Meeeeee, M. M.; Meeeee, M. M.; Meeeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [306] | Meeeee, M. M.; Meeeee, M., M. Me. Meee. Mee., (8888) 88, 888. |
| [307] | Meeeee, M. M.; Meeeee, M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [308] | Meeeeeeeee, M. M.; Meeee, M. M.; Meeeeeeeeee, M. M., Mee. Meee. Meeee., (8888) 8, 888. |
| [309] | Meeeeee, M.; Meeeeeee, M.; Meeeeeeee, M., Meee. Meee., (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8e, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 88.
- 8.Meeeee-Meee, (8888) M 88-8, 88.
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