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Please login to access the full content or check if you have access via43.8.3.1.2.3 Variation 3: With an Iodoalkane
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Aitken, R. A.; Aitken, K., Science of Synthesis, (2008) 43, 589.
The reactions of sodium acetylides with iodoalkanes resemble closely those with bromoalkanes; examples are presented in Table 12.[162–169]
Meeee 88 Meeeeeeee ee Meeeee Meeeeeeeee eeee Meeeeeeeeee[888–888]
Meeeee | Meeeeeeeee | Meeeeeee eee Meeeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|
MeM≡MM | Me(MM8)8M | 8. MeMM8, MM8, eeeeee, 8 e 8. eeee eeee eeeeeeee ee eeeeee, eeeeee, 8 e |
88 | [888] |
Me(MM8)8M≡MM | Me(MM8)8M | 8. MeMM8, MM8, eeeeee,8 e 8. eeeeee, eeeeeeeee |
88 | [888] |
MM≡M(MM8)8M≡MM | MeM | 8. MeMM8, MM8/Me8M, −88°M, 8 e 8. −88°M, 8 e |
88e | [888] |
Me(MM8)8M | 8. MeMM8, MM8, 8.8 e 8. eeeeeeeee |
88 | [888] | |
MM≡MM | Me(MM8)8M | 8. MeMM8, MM8, eeeeee,8.8 e 8. eeeeee, 8 e |
88 | [888] |
MM≡MM | M(MM8)8MMe8MM8Me | MeMM8, MM8, eeeee ee eeee ee ee eeee 8 e | 88 | [888] |
MM≡MM | Me(MM8)8M | MeMM8, MM8, eeeeee, 8 e | 88 | [888] |
MM≡M(MM8)8M≡MM | MeM | 8. MeMM8, MM8/MMM, −88°M, 88 eee 8. −88°M, 8 e, eeee eeee ee ee |
88e | [888] |
e 8: Meeeeeeeee eee eeeeeeeeeeeee ee eeeeee; 8: Meeeeeeeee eeeeeeeeee. Meeeee eeeee eeeeeeeee eeeeee, eee eeeeeeeee ee eeeeee eeeeeee eee eeeeeeeee ee eee ee ee 88°M.
e Meeee ee eeeeeeeeeeeeee eeeeeee.
Mee eeeeeeeeeee eeeeeee eee eeeee ee Meeeee 88. Meeeeeee 88 ee eeeeeeee eeeee eeeeeeeeee eeeeee eeeee ee eeeeeeeeeeeeeee[888] eee eeeeeeee 88 eeeee eeeeee eeeeeee ee eee eeee.[888]
Meeeee 88 Meeeeeeeeeee ee Meeeee ee Meeeee Meeeeee eee Meeeeeeeeeeee Meeee Meeeeeeeeee[888,888]
Meeeeeeeeeee Meeeeeeee
88-(8,8,8,8-Meeeeeeeeeee-8-eeeeeeeeeeee)eeeeee-8,8-eeee-8-ee (88); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeee eeeee eeeeeeeeee eeeeeee ee eeeeeeee ee eeeeeee ee eeeeeeee ee eee eee eee eeee ee e eeeeee eeeeeeee.
MMMMMMM: Meeeeeeeeeeeeeeeeeee eeeeeeee ee e eeeeeeee eeeee eeeeeeeeee eee ee eee eee eeee eeeeeeee.
Me e eeeeeee eeee ee MeMM8 (8.88 e, 88 eeee) ee MMM (88 eM) ee ee eee eeeee eeeeeeee M-(eeeeeeeeee-8M-eeeee-8-ee)eeee-8,8-eeee-8-ee (8.88 e, 88 eeee) ee MMM (88 eM) eeee 88 eee. Mee eeeeeee eee eeeeeee ee 88°M eee 8.8 e eee eeee eeeeee ee −8°M eee MMMM (8 eM) eee eeeee, eeeeeeee ee 8-(8-eeeeeeeee)-8,8,8,8-eeeeeeeeeeee-8-eeeeeeeeeeeee (8.8 e, 88 eeee) ee MMM (88 eM) eeee 88 eee. Mee eeeeeee eee eeeeeee ee ee eee 8 e, eeeee eeeee MM8Me (8.8 e) eee M8M (88 eM) eeee eeeee. Mee MMM eee eeeeeeeeee eee eee eeeeeee eee eeeeeeeee ee Me8M, eeeeee, eeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeeee ee MeMM eee MeMM (8.88 e, 8.8 eeee) eee eeeee. Mee eeeeeee eee eeeeee ee 88°M eee 88 eee eee eeee eeeeeee ee eeee ee ee eee MeMMM8 (8.8 e) eee eeeee. Mee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eeeeee ee eeee Me8M ee eeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eMe8M); eeeee: 8.88 e (88%).
Meeee-8,8-eeeee (88); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeeeeeeeeeeeeeee eeeeeeee ee e eeeeeeee eeeee eeeeeeeeee eee ee eee eee eeee eeeeeeee.
MMMMMMM: Meeeeeeeee, eeeeeeeee, ee eeee eeeeeeeeee ee eeeeeeeeeee eee ee eeeee.
Me e eeeeeeeeee ee eeeeeee-eeeeee MeM (8.88 e, 8.888 eee) ee eee MMM (888 eM) eee eeeee eeee-8,8-eeeee (8 e, 8.8 eM, 8.888 eee), MMMM (8.88 e, 8.8 eM, 8.888 eee), eee MeM (88 e, 88 eM, 8.888 eee). Meeee 88 e, M8M (888 eM) eee eeeee eee eee eeeeeee eee eeeeeeeee eeee eeeeeee. Mee eeeeeee eeee eee eeeeeeeee ee eeee, eeeee eeeeeee, eeeeee 88 ee e eeeeee; eeeee: 8.88 e (88%); ee 88–88°M/888 Meee; eeeeeeee ee eeee-8,8-eeeee; eeeee: 8.88 e (88%); ee 88–88°M/88 Meee.
References
[162] | Meeee, M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[163] | Meeee, M.; Meeeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[164] | Meeeeee, M. M.; Meeeeeeeee, M., M. Meee. Mee., (8888), 888. |
[165] | Meeeeee, M.; Meeeeee, M. M., M. Meee. Mee., (8888), 8888. |
[166] | Meeeeee, M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[167] | Meeee, M. M.; MeMeee, M. M., M. Meee. Mee., (8888), 8888. |
[168] | Meeeeeee, M. M.; Meeee, M. M., M. Meee. Mee., (8888), 8888. |
[169] | Meeeee, M.; Meee, M.; Mäe, M.; Meeeee, M., Meee. Meee. Meee, (8888) 88, 8888. |
[170] | Meeeeeeee, M.; Meeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[171] | Meeee, M. M.; Meee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.