Chemo- and diastereoselective epoxidation of allylic alcohols with a titania–silica aerogel

作者: M. Dusi , T. Mallat , A. Baiker

DOI: 10.1016/S1381-1169(98)00150-2

关键词:

摘要: Abstract An amorphous mesoporous titania–silica aerogel (20 wt.% TiO 2 –80 SiO ) and tert -butylhydroperoxide have been used for the epoxidation of various allylic alcohols. Cyclic alcohols alkenols possessing an internal double bond were more reactive than with a terminal CC bond. Epoxide selectivities could be improved by catalyst pre-drying hydrophobisation in toluene, as well addition (basic) zeolite 4A NaHCO 3 to reaction mixture. Diastereoselective cyclic yielded preferentially cis -epoxides. The performance α-β-unsaturated carbonyl compounds was compared those titania-on-silica TS-1. Interestingly, TS-1 inactive compounds.

参考文章(24)
R. Hutter, T. Mallat, A. Baiker, Titania-Silica Mixed Oxides: III. Epoxidation of α-Isophorone with Hydroperoxides Journal of Catalysis. ,vol. 157, pp. 665- 675 ,(1995) , 10.1006/JCAT.1995.1332
D.C.M. Dutoit, U. Göbel, M. Schneider, A. Baiker, Titania–Silica Mixed Oxides: V. Effect of Sol-Gel and Drying Conditions on Surface Properties Journal of Catalysis. ,vol. 164, pp. 433- 439 ,(1996) , 10.1006/JCAT.1996.0399
D.C.M. Dutoit, M. Schneider, R. Hutter, A. Baiker, Titania–Silica Mixed Oxides: IV. Influence of Ti Content and Aging on Structural and Catalytic Properties of Aerogels Journal of Catalysis. ,vol. 161, pp. 651- 658 ,(1996) , 10.1006/JCAT.1996.0227
Takashi Tatsumi, Makoto Yako, Makoto Nakamura, Yoshimitsu Yuhara, Hiro-o Tominaga, Effect of alkene structure on selectivity in the oxidation of unsaturated alcohols with titanium silicalite-1 catalyst Journal of Molecular Catalysis. ,vol. 78, pp. L41- L45 ,(1993) , 10.1016/0304-5102(93)87052-A
Goran Magnusson, Svante Thoren, New route to cyclopentene-1-carboxaldehydes by rearrangement of 2,3-epoxycyclohexanols The Journal of Organic Chemistry. ,vol. 38, pp. 1380- 1384 ,(1973) , 10.1021/JO00947A030
Hafedh Kochkar, François Figueras, Synthesis of Hydrophobic TiO2–SiO2Mixed Oxides for the Epoxidation of Cyclohexene Journal of Catalysis. ,vol. 171, pp. 420- 430 ,(1997) , 10.1006/JCAT.1997.1820
Stephan Klein, Johan A. Martens, Rudi Parton, Karen Vercruysse, Pierre A. Jacobs, Wilhelm F. Maier, Amorphous microporous mixed oxides as selective redox catalysts Catalysis Letters. ,vol. 38, pp. 209- 214 ,(1996) , 10.1007/BF00806570
Laura Palombi, Francesco Bonadies, Arrigo Scettri, Diastereoselective epoxidation of allylic alcohols by t-butyl hydroperoxide/zeolites system Tetrahedron. ,vol. 53, pp. 11369- 11376 ,(1997) , 10.1016/S0040-4020(97)00718-7
R. Hutter, T. Mallat, A. Peterhans, A. Baiker, Epoxidation of β-isophorone over a titania-silica aerogel : Effect of catalyst pretreatments with bases Journal of Catalysis. ,vol. 172, pp. 427- 435 ,(1997) , 10.1006/JCAT.1997.1822
Serge Thorimbert, Stephan Klein, Wilhelm F. Maier, Selective heterogeneous epoxidations with Cp-titanium chloride derived microporous silica glasses Tetrahedron. ,vol. 51, pp. 3787- 3792 ,(1995) , 10.1016/0040-4020(95)00123-P