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Tidwell, T. T., Science of Synthesis, (2006) 23, 571.
Monoalkylketenes are typically generated by dehydrohalogenation of acyl chlorides,[24–31] dehalogenation of α-haloacyl halides,[1,32,33] or Wolff rearrangements.[17,19] Butylketene can be obtained in solution for kinetic studies by photolysis of cyclohexanone.[34] All monoalkylketenes are prone to dimerization, and in the case of dehydrochlorination at elevated temperatures in solution, only the ketene dimers are isolated,[24–28] although the ketenes can be trapped by means of cycloaddition reactions.[29–31] Both methylene-β-lactone dimers and cyclobutane-1,3-dione dimers are known. The structures of the lactone dimer 11 and the enolized diketone dimer 12 from methylketene (1) were established in 1950 by Woodward and Small (Scheme 3).[35] The formation of lactone dimers is favored in dehydrochlorination reactions of acyl chlorides with triethylamine (Scheme 3),[24–27] and it has been suggested that their formation is catalyzed by triethylamine hydrochloride, whereas the uncatalyzed reaction leads to cyclobutane-1,3-dione dimers.[36]
Meeeee 8 Meeeeeeeeeee ee Meeeeeeeeeeeeeee Me Meee Meeeeeeee-β-eeeeeeee eee Meeeeeeeeeeeeeeee[88–88]
References
| [1] | Meeeeeeeee, M.; Meeeee, M. M., Mee. Meeee. Meee. Mee., (8888) 88, 888. |
| [17] | Meeee-Meeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [19] | Meeeeee, M.; Meeeeeee, M.; Meeeeeeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeee, M.-M., Meeee, M., M. Mee. Meee., (8888) 88, 888. |
| [24] | Meeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [25] | Meee, M. M.; Meeeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [26] | Meeeeee, M. M.; Meeee, M. M., Mee. Meeee. (M. M.), (8888) 8, 888. |
| [27] | Meeee, M. M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
| [28] | Meeeeee, M. M.; Meeeeeeee, M., Meeee. Meeeee., (8888) 88, 88. |
| [29] | Mee, M.; Meeeeee, M.; Meeeeeeeeeeee, M.; Meeeeeee, M. M., Meee. Meee. Meee, (8888) 88, 888. |
| [30] | Meeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [31] | Meeeeeeeeee, M.; Meeeee, M., Meee. Mee., (8888) 88, 8888. |
| [32] | MeMeeeee, M. M.; Meee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [33] | Meeeeee, M. M.; Meeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [34] | Meeee, M. M.; Meeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., Mee. M. Meee., (8888) 88, 8888. |
| [35] | Meeeeeee, M. M.; Meeee, M., Me., M. Me. Meee. Mee., (8888) 88, 8888. |
| [36] | Meeeee, M. M.; Meeeeee, M. M.; Meee, M. M.; Meeeeeee, M. M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8, 88.
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
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