Carbodiimide-promoted epoxidation of olefins

Details Carbodiimide-promoted epoxidation of olefins Carbodiimide-promoted epoxidation of olefins

1997-03-06

1998-09-15

Trinh, Ba K.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30112

Patent

active

058081151

ABSTRACT:
A method is provided for oxidizing an olefin to an epoxide by treating the olefin with hydrogen peroxide and a carbodiimide in the presence of an acid or base in a solvent system comprising a protic solvent. More specifically, a method is provided for oxidizing an olefin to an epoxide by contacting the olefin with aqueous hydrogen peroxide and a carbodiimide in the presence of a mild acid or mild base in a solvent system comprising a protic solvent.

REFERENCES:
patent: 4471130 (1984-09-01), Katsuki et al.
patent: 4594439 (1986-06-01), Katsuki et al.
Payne, G. et al. (1961), "Reactions of Hydrogen Peroxide. VII. Alkali-Catalyzed Epoxidation and Oxidation Using a Nitrile as Co-reactant," J. Org. Chem. 26:659-663.
Venturello, C. et al. (1983), "A New, Effective Catalytic System of Epoxidation of Olefins by Hydrogen Peroxide under Phase-Transfer Conditions," J. Org. Chem. 48:3831-3833.
Reynaud et al. (1985), "A Very Efficient System for Alkene Epoxidation by Hydrogen Peroxide: Catalysis by Manganese-Porphyrins in the Presence of Imidazole," J. Chem. Soc. Chem. Commun., pp. 888-889.
Rebek, J., Jr. and McCready, R. (1979), "A New Class of Epoxidation Reagents," Tet. Lett. No. 12, pp. 1001-1002.
Rebek, J., Jr. and McCready, R. (1980), "Intramolecular epoxidation with the hydrogen peroxide/orthoester system" Tet. Lett. 21(26):2491-2492.
Rebek, J., Jr. and McCready, R. (1979), "New Epoxidation Reagents Dervied from Alumina and Silicon," Tet. Lett. No. 45, pp. 4337-4338.
Rebek, J., Jr. et al. (1980), "Olefin Epoxidation with .alpha.-Hydroperoxides of Esters, Amides, Ketones, and Nitriles," J. Chem. Soc. Chem. Commun., pp. 705-706.
Heggs, R. and Ganem, B. (1979), "2-Hydroperoxyhexafluoro-2-propanol. A Low-Cost, Catalytic Oxidant for Synthesis and a Structural Analogue of Naturally Occurring Flavin Hydroperoxides," J. Am. Chem. Soc. 101:2484-2486.
Chen, Y. and Reymond, J.-L. (1995), "Epoxidation of Olefins with Formamide--Hydrogen Peroxide," Tet. Let. 36(23):4015-4018.
Krishnan, S. (1977), "The Formation of Arene Oxides by Direct Oxidation of Arenes Using Carbodiimides and Hydrogen Peroxide," Tet. Lett. No. 16, pp. 1369-1372.
Rebek, J., Jr. et al. (1974), "Substituted Peroxycarbamic Acids as Epoxidizing Agents," J. Chem. Soc. Chem. Commun., p. 711.
Matsumura et al. (1970), "Epoxidation of Olefins with Hydrogen Peroxide Using an Isocyanate as Co-reactant," Tet. Lett. No. 23, pp. 2029-2032.
Rebek, J., et al., (1976), "Epoxidation and Singlet Oxygen Generation From Dehydrating Agents and Hydrogen Peroxide," Abstracts of the 172nd National Meeting of the American Chemical Society, ORGN 109.
Rebek et al. (1979), "New Oxidizing Agents from the Dehydration of Hydrogen Peroxide,"J. Org. Chem. 44(9):1485-1493.
Adamczyk et al. (1995), "An Easy Preparation of Hapten Active Esters via Solid Supported EDAC," Tet. Lett. 36(46):8345-8346.
Desai, M. and Stramiello, L. (1993), "Polymer Bound EDC (P-EDC): A Convenient Reagent for Formation of an Amide Bond," Tet. Lett., 34(48):7685-7688.
Henbest, H.B.; Wilson, R.A.L. (1957), "Aspects of Stereochemistry. Part I. Stereospecificity in Formation of Epoxides from Cyclic Allylic Alcohols," J. Chem. Soc., pp. 1958-1965.
March Advanced Organic Chemistry, 4th ed. Wiley, NY, (1992), pp. 826-829.
Garside, P. et al. (1969), "Action of Peracetic Acid on (+) Sabinol," J. Chem. Soc. C, pp. 716-721.
Majetich, G. and Hicks, R. (1995), "Carbodiimide Mediated Epoxidation of Olefins with Aqueous Hydrogen Peroxide," Thirty-Fourth Natl. Organic Symp., The College of William and Mary, Williamsburg, Virginia, Jun. 11-15, 1995, Abstract #80.
Wolf, S.F., (1977), "Epoxidation and Singlet Oxygen Generation from Dehydrating Agents and Hydrogen Peroxide," Ph.D. Thesis, University of California, Los Angeles.

Affiliated with

Also associated with

Rating

Carbodiimide-promoted epoxidation of olefins does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Carbodiimide-promoted epoxidation of olefins, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Carbodiimide-promoted epoxidation of olefins will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-89703