Organic reactions catalyzed by methylrhenium trioxide: Dehydration, amination, and disproportionation of alcohols
- Iowa State Univ., Ames, IA (United States)
Methylrhenium trioxide (MTO) is the first transition metal complex in trace quantity to catalyze the direct formation of ethers from alcohols. The reactions are independent of the solvents used: benzene, toluene, dichloromethane, chloroform, acetone, and in the alcohols themselves. Aromatic alcohols gave better yields than aliphatic. Reactions between two different alcohols could also be used to prepare unsymmetric ethers, the best yields being obtained when one of the alcohols is aromatic alcohols proceeding in better yield. When primary (secondary) amines were used as the limiting reagent, direct amination of alcohols catalyzed by MTO gave good yields of the expected secondary (tertiary) amines at room temperature. Disproportionation of alcohols to alkanes and carbonyl compounds was also observed for aromatic alcohols in the presence of MTO. On the basis of the results of this investigation and a comparison with the interaction between MTO and water, a concerted process and a mechanism involving carbocation intermediates have been suggested. 5 tabs.
- OSTI ID:
- 427057
- Journal Information:
- Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 1 Vol. 61; ISSN 0022-3263; ISSN JOCEAH
- Country of Publication:
- United States
- Language:
- English
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