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Synthesis and catalytic activity of binuclear Mn (III, III) –BINOL complexes for epoxidation of olefins
Author(s) -
Patel Mitesh J.,
Trivedi Bhavna M.
Publication year - 2006
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1081
Subject(s) - chemistry , catalysis , epoxide , solvent , enantioselective synthesis , styrene , peroxide , polymer chemistry , organic chemistry , medicinal chemistry , copolymer , polymer
The novel binuclear complexes [Mn 2 (III, III) (BINOL) 3 L 2 ]2H 2 O, where, L = 2, 2′‐bipyridine (Bpy) or 1,10‐phenanthroline (Phen) and BINOL = 1, 1′‐bi‐2‐naphthol were synthesized and characterized by elemental analyses, magnetic susceptibility and various spectral methods. The catalytic activity of these complexes was studied for the epoxidation reaction of unfunctionalized olefins like styrene, 1‐hexene, 1‐octene and 1‐decene. The products thus obtained were analyzed by GC. The epoxidation reactions were carried out, in the presence of catalyst with different oxidants, to study the effect of the nature of the oxidant on the reactions. The different oxidants used were the peroxide oxygen donor (e.g. TBHP and H 2 O 2 ), mono oxygen donor (e.g. PhIO) and dioxygen donor (e.g. molecular O 2 ). TBHP was found to be the best oxidant for the epoxidation reaction. To study the effect of the solvent on the epoxidation, the reactions were carried out in different media, such as a polar media (e.g. with CH 3 OH as solvent), non‐polar media (e.g. with CH 2 Cl 2 and C 6 H 6 as solvents) and coordinating solvent (e.g. CH 3 CN). The maximum epoxide formation was observed in CH 2 Cl 2 medium. The epoxidation reactions with optically active BINOL catalysts under optimum established conditions were carried out to examine the enantioselectivity of the catalysts. The complexes were, however, found not to be enantioselective. Copyright © 2006 John Wiley & Sons, Ltd.