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Krueger, A., Science of Synthesis, (2008) 43, 544.
Related to the reaction of cyclopropylcarbenes is the rearrangement of cyclopropenylcarbenes, several examples having been described in the literature (Scheme 78).[297–299] Usually the carbene is produced by the fragmentation of diazomethane derivatives or directly from tosylhydrazones. The product mixture of the rearrangement consists of the two alkynes formed by the fragmentation. However, there is no clear evidence that the cyclopropenylcarbene rearrangement (by analogy to the cyclopropylcarbene reaction) is really a coarctate reaction or not.[263] Computational studies show that the reaction does not proceed in a synchronized fashion and that the transition state is unsymmetrical and possesses a strong diradical character.
Meeeee 88 Meeeeeeeeeeeeeeeeeee Meeeeeeeeeeee[888–888]
| Meeeeeee | Meeeeee | Meeeeeeeee | Meeeee (%) | Mee |
|---|---|---|---|---|
 |
MM≡MM | 888°M, eeeeee eeee (−888°M) | 88–88 | [888] |
| |
MeM≡MMe | eeee ee eν, −88°M | 88–88 | [888] |
| |
MeM≡MMe | 8. MeMMe, MeMM 8. ee ee 88°M, 88−8 Meee, 8 e |
e.e. | [888] |
| |
MMMM≡MMMM | 8. MeMe 8. 888°M 8. eν (888 ee), 88 M |
e.e. | [888] |
e e.e. = eee eeeeeeee.
M eeeeeeeee ee eee eeeeeeeeeeeeeeeeeeee eeeeeeeeeeeee ee eee eeeeeeee ee eee eeeeeeeeee eeeeeeeeeeeeeeeeeeeee. Meee eee eeeeeeee eeee eee eeeeee eee eeeee ee eeeeee eee e eeeeeee eeeee eee eeeeeeeeeeeee (Meeeee 88).[888–888]
Meeeee 88 Meeeeeeeeeeeeeeeeeee Meeeeeeeeeeee[888–888]
| M8 | Meeeeeeeee | Meeeee (%) | Mee |
|---|---|---|---|
| e-Me | eeeeeee, eν (>888 ee), 88°M | eeeee | [888] |
| e-Me | eeeee eeeeee, eν (888, 888 ee) | e.e. | [888] |
| Me | MM8Me8 (ee eeeeeee), 8888-M Me eeee, ee | e.e. | [888] |
e e.e. = eee eeeeeeee.
Meeeeee eee eeeeeee eeeeeeeee eeeeeeeeeee-8-eeeeeeeeee eee -eeeeeeee, eeeeeeeeeee-8-ee eeeeeeeeeee eee eeee eeeeeeeee ee ee eeeeee. Meee eeeeeeee eee eeee eeeeeeeee ee Meeeee ee e eeeee eeeeeeeeeee eeeeeeee eee eeeeeeeeee eeeeeeeeeeeeee eeeeeeee.[888,888] Mee eeeeeeeee ee (8,8,8-eeeeeeeeeeeeeeeeee-8-eeee)eeeeeee eee eeeeeeee eeeeeeeee ee Meeee ee ee.[888–888] Mee eeeeeeeeee eeeeeeee eeee eeeeeeeeeeeeeeeee eeeeee e eeeeeeeee, eeeee eeeeeeeeee eeee e eeeeeeeeeeeeee (8,8-eeeeeeeeeeee-8-ee-8-eee).[888] Meeeeee eeeeeeeeeee eeeeeeee ee eee eeeeeeeeeeeee ee eee eeeeeeeeee eeeeeeeeeeeeeee ee e Meeeeee–Meeeeee eeeeeeee. Mee eeeeeeeeeeee eeeeeee eeeeeee eeeeeeeeee eeee eee eeeeeeeeee eeeeeeeeeeeeee (Meeeee 88).[888]
Meeeee 88 Meeeeeeee ee 8,8,8-Meeeeeeeeeee-8-ee-8-eee[888]
References
| [263] | Meeeee, M., Meeee. Meee., (8888) 888, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
| [297] | Meeeeeee, M. M.; Mee, M.-M., M. Me. Meee. Mee., (8888) 88, 888. |
| [298] | Meeee, M. M.; Meeeee, M. M. M.; Meeeee, M.; Meeeeeee, M.; Meeeee, M. M.; Meeeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeeeeee, M. M.; Meeee, M., Meee. Mee., (8888) 888, 8888. |
| [299] | Meeee, M.; Meeee, M.; Meeeeeeeee, M. M.; Meüeee, M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
| [300] | Meeeeeeeeee, M.-M.; Meeeee, M.; Meeeee, M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
| [301] | Meeee, M.; Meeäeee, M., Meeeeee Mee. Meee., (8888), 888. |
| [302] | Meeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [303] | Meeeee, M., M. Meee. Mee. Meeeee. Mee., (8888) 88, 888. |
| [304] | Meeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [305] | Meeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 88, 88. |
| [306] | Meeee, M. M.; Meeee, M. M.; Möee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
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