| Identification | Back Directory | [Name]
Dimethylaluminum Amide | [CAS]
24758-44-9 | [Synonyms]
Dimethylaluminum Amide
dimethylaluminium amide | [Molecular Formula]
C2H8AlN | [MDL Number]
MFCD16876561 | [MOL File]
24758-44-9.mol | [Molecular Weight]
73.07 |
| Hazard Information | Back Directory | [Chemical Properties]
Dialkylaluminum amides are hydrolytically unstable. 1 M stock solutions can be prepared and stored in the freezer, although the best results are usually obtained with freshly prepared reagents. Dialkylaluminum amides are commonly prepared in situ. Dimethylaluminum amide exists as a six-membered ring trimer in the solid state.
| [Uses]
Dimethylaluminum Amide is a mild, nonbasic amine transfer reagent compatible with many functional groups.
| [Synthesis]
Dialkylaluminum amides are conveniently prepared in situ from the appropriate trialkylaluminum and amine or amine hydrochloride.
| [References]
1. Lipton, M. F.; Basha, A.; Weinreb, S. M. OSC 1988, 6, 492.
2. (a) Mole, T.; Jeffery, E. A. Organoaluminium Compounds; Elsevier: New York, 1972; Chapter 9. (b) Hauske, J. R. COS 1991, 1, Chapter 1.3. (c) Interrante, L. V.; Carpenter, L. E.; Whitmarsh, C.; Lee, W.; Garbauskas, M.; Slack, G. A. Mater. Res. Soc. Symp. Proc. 1986, 73.
3. Basha, A.; Lipton, M.; Weinreb, S. M. TL 1977, 4171.
4. (a) Levin, J. I.; Turos, E.; Weinreb, S. M. SC 1982, 12, 989. (b) Sidler, D. R.; Lovelace, T. C.; McNamara, J. M.; Reider, P. J. JOC 1994, 59, 1231. |
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