Reactions of ethyl diazoacetate catalyzed by methylrhenium trioxide
- Iowa State Univ., Ames, IA (United States)
Methylrhenium trioxide (CH{sub 3}ReO{sub 3} or MTO) has found wise use in catalysis, including the epoxidation and metathesis of olefins, aldehyde olefination, and oxygen transfer. Extensive reports have now appeared in the area of MTO-catalyzed substrate oxidations with hydrogen peroxide. Certain catalytic applications of MTO for organic reactions that do not utilize peroxide have now been realized. In particular, a catalytic amount of MTO with ethyl diazoacetate (EDA) will convert aromatic imines to aziridines and convert aldehydes and ketones to epoxides. The aziridine preparation proceeds in high yields under anaerobic conditions more conveniently than with existing methods. Compounds with a three-membered heterocyclic ring can be obtained with the EDA/MTO catalytic system. Aromatic imines undergo cycloaddition reactions to give aziridines under mild conditions.
- DOE Contract Number:
- W-7405-ENG-82
- OSTI ID:
- 183495
- Journal Information:
- Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 22 Vol. 60; ISSN JOCEAH; ISSN 0022-3263
- Country of Publication:
- United States
- Language:
- English
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