Process for the epoxidation of olefins with hydrogen peroxide catalyzed ruthenium.

摘要

Process for the preparation of compounds of formula (I), (See formula) wherein R 1, R 2, R 3 and R 4 represent each independently hydrogen, alkyl, aryl, arylalkyl, haloalkyl or moieties of formula (IIa ) to (IIf) (See formulas) wherein in formulas (IIa) to (IIf) a is absent or represents an alkylene or haloalkylene moiety and B is missing or represents oxygen or NR 5 R 5 represents hydrogen, arylalkyl or aryl and D represents a carbonyl group and E represents R 6, oR 6, NHR 7 or N (R 7) 2 wherein R 6 represents alkyl, arylalkyl or aryl and R 7 is each independently alkyl, arylalkyl or aryl or N (R 7) 2 together represents a cyclic amino radical having 4 to 12 carbon atoms and W represents OH, NH2 or OM, M being an alkali metal ion, one half equivalent of an alkaline earth metal ion, an ammonium ion or an ammonium ion organic or respectively two of the radicals R 1, R 2, R 3 and R 4 together are p art of a 3- to 7-membered in total comprising 3 to 16 carbon atoms, which is characterized in that compounds of formula (III), (see formula) wherein R 1, R 2, R 3 and R 4 have each independently as defined above, with hydrogen peroxide, the reaction being effected in the presence of a ruthenium complex as ligands leads both compounds of formula (IV) (see formula) wherein R 8, R 9, R 10, R 11, R 12, R 13, R 14, R 15, R 16, R 17 and R 18 represent each independently hydrogen, halogen, hydroxy, hydroxycarbonyl, alkoxycarbonyl, alkoxy, alkyl, arylalkyl or aryl or respectively two of the radicals R 8, R 9, R 10 and R 11 or respectively two of the radicals R 15, R 16, R 17 and R 18 are together part of a monocyclic 3- to 7-membered in total comprising from 3 to 16 carbon atoms, or together are part of a bicycle total comprising 3 to 16 carbon atoms, and also compounds of formula (V) (see formula) wherein X 1, X 2 and X 3 represent each independently N, CH or CR 19 and R 19 represents hydrogen, halogen , hydroxy, hydroxycarbonyl, alkoxycarbonyl, alkoxy, alkoxyalkyl, arylalkyl or aryl and n represents 0, 1, 2 or 3, preferably 0 or 1 and particularly preferably 0.