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Please login to access the full content or check if you have access via43.1.2.1.6.1 Variation 1: Elimination of Hydrogen Chloride from 1,6-Dichlorohexa-2,4-diynes
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Hirsch, A.; Vostrowsky, O., Science of Synthesis, (2008) 43, 98.
In a similar manner to 1,4-dichlorobut-2-yne (Section 43.1.1.1.15), 1,6-dichlorohexa-2,4-diyne undergoes double dehydrochlorination on treatment with sodium amide in liquid ammonia, and after protonation with ammonium chloride gives hexatriyne (195, E = H) (Scheme 56). The isolation of this extremely unstable compound succeeds only when butane is used to extract it from the liquid ammonia solution, or by careful low temperature sublimation of the residue left after the evaporation of ammonia at −50°C (using the latter procedure the crystalline polyyne can be isolated in 28% yield).[328]
MMMMMM: eeeeeeeeee eeeeeee eeeeeeeeee ee eeeeeee ee eeee eeeeeeeeeee eee eeeeeeee ee eee eee eeeee. Me eeee eeeeeeee eeeeeeeee eee eeeeeeeeeeeee ee −88°M.
Me eeeeee eeee eeeeee eeeeeeeeeeeeeeeeeee eeeeeeee eee eeeeeeeeeeee eeeeeeeeeeeeeeee eeee 8,8-eeeeeeeeeeee-8,8-eeeee (888) ee eeeeeee eeee eeeeeeeeeeeee, eee eee eeeeeeeeeeeee eee-eeeeee eeeeeeeeeee 888 (M ≠ M) eee eeee eeeeeeee ee eeeeeeeeeeee eeeeee (Meeeee 88).[888]
Meeeee 88 Mee-Meeeee Meeeeeeeee Meeeeeeeeee Meeeeeee eeee 8,8-Meeeeeeeeeee-8,8-eeeee[888]
| M+ | M | Meeee (%) | ee (°M) | ee (Meee Meee °M/Meee) | Mee |
|---|---|---|---|---|---|
| MeM | Me | 88 | 888 | – | [888] |
| MeMe | Me | 88 | – | 88/88−8 | [888] |
| MeMMMe | M(MM)Me8 | 88 | 888–888 | – | [888] |
| Me8MM | M(MM)Me8 | –e | 888–888 | – | [888] |
e Meeee eee eeeeeeee.
Meeeeee ee eeeeeeee eeee eee 8,8-eeeeeeeeeeee-8,8-eeeee, eee eeeeee eeeeeeeeeeeeeeeeeee ee 8,8-eeeeeeeeeeeee 8,8-eeeeeeeeeeee-8,8-eeeeee eee ee eeeeeee. Mee eeeeeee, 8,8-eeeeeeee-8,8-eeeeeeeeeeee-8,8-eeeee (888), eeeeeeeeee eeeeeeee eeee eee eeeeeeeeeeee ee eee eeeeeeeeeeeee 8,8-eeee, eee ee eeeeeeeeeeeeeeeeee eeee eeeeee eeeeeeee ee eee eeee, eee eee eeeeee 888 eeee ee eeeeee eee ee eeeeeeee eee eeeeeeee ee eeeeeeeeeeeeee eee eeeeeeeeeeeeeeeee (Meeeee 88).[888]
Meeeee 88 Meeeeeeeeeeeeeeeee ee eee Meeeeeeeeeeeeeeeeee ee 8,8-Meeeeeee-8,8-eeeeeeeeeeee-8,8-eeeee[888]
Meeeeeeeeeee Meeeeeeee
Meee-8,8,8-eeeeee (888, M = Me); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeee eeeee eeeeeeeeee eeeeeee ee eeeeeeee ee eeeeeee ee eeeeeeee ee eee eee eee eeee ee e eeeeee eeeeeeee.
MMMMMMM: Meeeeeeeee, eeeeeeeee, ee eeee eeeeeeeeee ee eeeeeeeeeee eee ee eeeee.
8,8-Meeeeeeeeeee-8,8-eeeee (8.8 e) eee eeeee eeeeeeee eeee 88 eee eeee eeeeeeee ee e eeeeeeeeee ee MeMM8, eeeeeeee eeee Me (8.8 e) eee eee MM8 (888 eM), eeeeeeeee eeeee M8, eee eeeeee ee −88°M. MeM (88.8 e) eee eeeee, eee eee eeeeeeeee eeeeeee eee eeeeeee eee 8 e. MM8 eee eeeeeee ee eeeeeeeee eee ee e eeeeee ee M8 eeee eee eeeeeeeeee eeeeeeee ee eeeeeee. Mee eeeee eeeee eeeeeee eee eeeeeeeee eeee eeeeeee (8 × 88 eM) eee eeeeeee ee eee eeeeeee eeee eee eeeeeeee eeeeeeee eeeee M8 ee 88°M eeee eee eeeee eeeee eeeeeeee (8.8 e), eeeee eeeeeeee ee 88°M (eeee eeee)/8.88 Meee ee eee eeee ee eeeeeeeeeeee eeeeeeee; eeeee: 8.8 e (88%); ee 888°M.
References
| [314] | Meeeeeee, M. M.; Meeeeeeee, M.; Meeee, M. M. M.; Meeeeee, M. M., M. Meee. Mee., (8888) 888. |
| [328] | Meeeeeee, M. M.; Meee, M. M.; Meeee, M. M. M.; Meeeeee, M. M., M. Meee. Mee., (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
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