A simple and efficient method for epoxidation of terminal alkenes

Chemical Communications

Volumn , Issue 16, 1997, Pages 1565-1566

  Copéret, Christophe ^a   Adolfsson, Hans ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038285341     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a703542j     Document Type: Article

References (25)

1. Terminal alkenes are much less reactive, and only few reactions give good conversion. (a) For seminal papers and some recent advances in epoxidation of alkenes other than the MTO-catalysed ones, see G. Berti, F. Bottari, B. Macchia and F. Macchia, Tetrahedron, 1965, 21, 3277; G. Venturello, E. Alneri and M. Ricci, J. Org. Chem., 1983, 48, 3831; C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553; J. Prandi, H. B. Kagan and H. Mimoun, Tetrahedron Lett., 1986, 27, 2617; W. Adam and A. K. Smerz, J. Org. Chem., 1996, 61, 3506; R. W. Murray and M. Singh, Org Synth., 1996, 74, 91; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto and R. Noyori, J. Org. Chem., 1996, 61, 8310; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, D. Paneyella and R. Noyori, Bull Soc. Chem. Jpn., 1997, 70, 905; R. Murugavel and H. W. Roesky, Angew. Chem., Int. Ed. Engl., 1997, 36, 477;
2. Terminal alkenes are much less reactive, and only few reactions give good conversion. (a) For seminal papers and some recent advances in epoxidation of alkenes other than the MTO-catalysed ones, see G. Berti, F. Bottari, B. Macchia and F. Macchia, Tetrahedron, 1965, 21, 3277; G. Venturello, E. Alneri and M. Ricci, J. Org. Chem., 1983, 48, 3831; C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553; J. Prandi, H. B. Kagan and H. Mimoun, Tetrahedron Lett., 1986, 27, 2617; W. Adam and A. K. Smerz, J. Org. Chem., 1996, 61, 3506; R. W. Murray and M. Singh, Org Synth., 1996, 74, 91; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto and R. Noyori, J. Org. Chem., 1996, 61, 8310; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, D. Paneyella and R. Noyori, Bull Soc. Chem. Jpn., 1997, 70, 905; R. Murugavel and H. W. Roesky, Angew. Chem., Int. Ed. Engl., 1997, 36, 477;
3. Terminal alkenes are much less reactive, and only few reactions give good conversion. (a) For seminal papers and some recent advances in epoxidation of alkenes other than the MTO-catalysed ones, see G. Berti, F. Bottari, B. Macchia and F. Macchia, Tetrahedron, 1965, 21, 3277; G. Venturello, E. Alneri and M. Ricci, J. Org. Chem., 1983, 48, 3831; C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553; J. Prandi, H. B. Kagan and H. Mimoun, Tetrahedron Lett., 1986, 27, 2617; W. Adam and A. K. Smerz, J. Org. Chem., 1996, 61, 3506; R. W. Murray and M. Singh, Org Synth., 1996, 74, 91; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto and R. Noyori, J. Org. Chem., 1996, 61, 8310; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, D. Paneyella and R. Noyori, Bull Soc. Chem. Jpn., 1997, 70, 905; R. Murugavel and H. W. Roesky, Angew. Chem., Int. Ed. Engl., 1997, 36, 477;
4. Terminal alkenes are much less reactive, and only few reactions give good conversion. (a) For seminal papers and some recent advances in epoxidation of alkenes other than the MTO-catalysed ones, see G. Berti, F. Bottari, B. Macchia and F. Macchia, Tetrahedron, 1965, 21, 3277; G. Venturello, E. Alneri and M. Ricci, J. Org. Chem., 1983, 48, 3831; C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553; J. Prandi, H. B. Kagan and H. Mimoun, Tetrahedron Lett., 1986, 27, 2617; W. Adam and A. K. Smerz, J. Org. Chem., 1996, 61, 3506; R. W. Murray and M. Singh, Org Synth., 1996, 74, 91; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto and R. Noyori, J. Org. Chem., 1996, 61, 8310; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, D. Paneyella and R. Noyori, Bull Soc. Chem. Jpn., 1997, 70, 905; R. Murugavel and H. W. Roesky, Angew. Chem., Int. Ed. Engl., 1997, 36, 477;
5. Terminal alkenes are much less reactive, and only few reactions give good conversion. (a) For seminal papers and some recent advances in epoxidation of alkenes other than the MTO-catalysed ones, see G. Berti, F. Bottari, B. Macchia and F. Macchia, Tetrahedron, 1965, 21, 3277; G. Venturello, E. Alneri and M. Ricci, J. Org. Chem., 1983, 48, 3831; C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553; J. Prandi, H. B. Kagan and H. Mimoun, Tetrahedron Lett., 1986, 27, 2617; W. Adam and A. K. Smerz, J. Org. Chem., 1996, 61, 3506; R. W. Murray and M. Singh, Org Synth., 1996, 74, 91; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto and R. Noyori, J. Org. Chem., 1996, 61, 8310; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, D. Paneyella and R. Noyori, Bull Soc. Chem. Jpn., 1997, 70, 905; R. Murugavel and H. W. Roesky, Angew. Chem., Int. Ed. Engl., 1997, 36, 477;
6. Terminal alkenes are much less reactive, and only few reactions give good conversion. (a) For seminal papers and some recent advances in epoxidation of alkenes other than the MTO-catalysed ones, see G. Berti, F. Bottari, B. Macchia and F. Macchia, Tetrahedron, 1965, 21, 3277; G. Venturello, E. Alneri and M. Ricci, J. Org. Chem., 1983, 48, 3831; C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553; J. Prandi, H. B. Kagan and H. Mimoun, Tetrahedron Lett., 1986, 27, 2617; W. Adam and A. K. Smerz, J. Org. Chem., 1996, 61, 3506; R. W. Murray and M. Singh, Org Synth., 1996, 74, 91; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto and R. Noyori, J. Org. Chem., 1996, 61, 8310; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, D. Paneyella and R. Noyori, Bull Soc. Chem. Jpn., 1997, 70, 905; R. Murugavel and H. W. Roesky, Angew. Chem., Int. Ed. Engl., 1997, 36, 477;
7. Terminal alkenes are much less reactive, and only few reactions give good conversion. (a) For seminal papers and some recent advances in epoxidation of alkenes other than the MTO-catalysed ones, see G. Berti, F. Bottari, B. Macchia and F. Macchia, Tetrahedron, 1965, 21, 3277; G. Venturello, E. Alneri and M. Ricci, J. Org. Chem., 1983, 48, 3831; C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553; J. Prandi, H. B. Kagan and H. Mimoun, Tetrahedron Lett., 1986, 27, 2617; W. Adam and A. K. Smerz, J. Org. Chem., 1996, 61, 3506; R. W. Murray and M. Singh, Org Synth., 1996, 74, 91; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto and R. Noyori, J. Org. Chem., 1996, 61, 8310; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, D. Paneyella and R. Noyori, Bull Soc. Chem. Jpn., 1997, 70, 905; R. Murugavel and H. W. Roesky, Angew. Chem., Int. Ed. Engl., 1997, 36, 477;
8. Terminal alkenes are much less reactive, and only few reactions give good conversion. (a) For seminal papers and some recent advances in epoxidation of alkenes other than the MTO-catalysed ones, see G. Berti, F. Bottari, B. Macchia and F. Macchia, Tetrahedron, 1965, 21, 3277; G. Venturello, E. Alneri and M. Ricci, J. Org. Chem., 1983, 48, 3831; C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553; J. Prandi, H. B. Kagan and H. Mimoun, Tetrahedron Lett., 1986, 27, 2617; W. Adam and A. K. Smerz, J. Org. Chem., 1996, 61, 3506; R. W. Murray and M. Singh, Org Synth., 1996, 74, 91; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto and R. Noyori, J. Org. Chem., 1996, 61, 8310; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, D. Paneyella and R. Noyori, Bull Soc. Chem. Jpn., 1997, 70, 905; R. Murugavel and H. W. Roesky, Angew. Chem., Int. Ed. Engl., 1997, 36, 477;
9. Terminal alkenes are much less reactive, and only few reactions give good conversion. (a) For seminal papers and some recent advances in epoxidation of alkenes other than the MTO-catalysed ones, see G. Berti, F. Bottari, B. Macchia and F. Macchia, Tetrahedron, 1965, 21, 3277; G. Venturello, E. Alneri and M. Ricci, J. Org. Chem., 1983, 48, 3831; C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553; J. Prandi, H. B. Kagan and H. Mimoun, Tetrahedron Lett., 1986, 27, 2617; W. Adam and A. K. Smerz, J. Org. Chem., 1996, 61, 3506; R. W. Murray and M. Singh, Org Synth., 1996, 74, 91; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto and R. Noyori, J. Org. Chem., 1996, 61, 8310; K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, D. Paneyella and R. Noyori, Bull Soc. Chem. Jpn., 1997, 70, 905; R. Murugavel and H. W. Roesky, Angew. Chem., Int. Ed. Engl., 1997, 36, 477;
10. (b) For MTO-catalysed epoxidation of alkenes, see Hoechst AG (W. A. Herrmann, D. W. Marz, J. G. Kuchler, G. Weichselbaumer and R. W. Fischer) DE 3,902,357, 1989; W. A. Herrmann, R. W. Fischer and D. W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; W. A. Herrmann, R. W. Fischer, M. U. Rauch and W. Scherer, J. Mol. Catal., 1994, 86, 243; A. M. Al-Ajlouni and J. H. Espenson, J. Am. Chem. Soc., 1995, 117, 9243; O. Pestovsky, R. van Eldik, P. Huston and J. H. Espenson, J. Chem. Soc., Dalton Trans. 2, 1995, 133; W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149; W. Adam and C. M. Mitchell, Angew. Chem., Int. Ed. Engl., 1996, 35, 533; T. R. Boelow and C. S. Spilling, Tetrahedron Lett., 1996, 37, 2717; A. M. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 1996, 61, 3969; W. A. Herrmann, J. D. G. Correia, M. U. Rauch, G. R. J. Artus and F. E. Kühn, J. Mol. Cat., 1997, 118, 33; ARCO Chemical Technology (G. L. Crocco, W. P. Shum, J. G. Zajacek and H. S. Kesling, Jr.) US 5,166,372, 1992;
11. (b) For MTO-catalysed epoxidation of alkenes, see Hoechst AG (W. A. Herrmann, D. W. Marz, J. G. Kuchler, G. Weichselbaumer and R. W. Fischer) DE 3,902,357, 1989; W. A. Herrmann, R. W. Fischer and D. W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; W. A. Herrmann, R. W. Fischer, M. U. Rauch and W. Scherer, J. Mol. Catal., 1994, 86, 243; A. M. Al-Ajlouni and J. H. Espenson, J. Am. Chem. Soc., 1995, 117, 9243; O. Pestovsky, R. van Eldik, P. Huston and J. H. Espenson, J. Chem. Soc., Dalton Trans. 2, 1995, 133; W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149; W. Adam and C. M. Mitchell, Angew. Chem., Int. Ed. Engl., 1996, 35, 533; T. R. Boelow and C. S. Spilling, Tetrahedron Lett., 1996, 37, 2717; A. M. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 1996, 61, 3969; W. A. Herrmann, J. D. G. Correia, M. U. Rauch, G. R. J. Artus and F. E. Kühn, J. Mol. Cat., 1997, 118, 33; ARCO Chemical Technology (G. L. Crocco, W. P. Shum, J. G. Zajacek and H. S. Kesling, Jr.) US 5,166,372, 1992;
12. (b) For MTO-catalysed epoxidation of alkenes, see Hoechst AG (W. A. Herrmann, D. W. Marz, J. G. Kuchler, G. Weichselbaumer and R. W. Fischer) DE 3,902,357, 1989; W. A. Herrmann, R. W. Fischer and D. W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; W. A. Herrmann, R. W. Fischer, M. U. Rauch and W. Scherer, J. Mol. Catal., 1994, 86, 243; A. M. Al-Ajlouni and J. H. Espenson, J. Am. Chem. Soc., 1995, 117, 9243; O. Pestovsky, R. van Eldik, P. Huston and J. H. Espenson, J. Chem. Soc., Dalton Trans. 2, 1995, 133; W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149; W. Adam and C. M. Mitchell, Angew. Chem., Int. Ed. Engl., 1996, 35, 533; T. R. Boelow and C. S. Spilling, Tetrahedron Lett., 1996, 37, 2717; A. M. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 1996, 61, 3969; W. A. Herrmann, J. D. G. Correia, M. U. Rauch, G. R. J. Artus and F. E. Kühn, J. Mol. Cat., 1997, 118, 33; ARCO Chemical Technology (G. L. Crocco, W. P. Shum, J. G. Zajacek and H. S. Kesling, Jr.) US 5,166,372, 1992;
13. (b) For MTO-catalysed epoxidation of alkenes, see Hoechst AG (W. A. Herrmann, D. W. Marz, J. G. Kuchler, G. Weichselbaumer and R. W. Fischer) DE 3,902,357, 1989; W. A. Herrmann, R. W. Fischer and D. W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; W. A. Herrmann, R. W. Fischer, M. U. Rauch and W. Scherer, J. Mol. Catal., 1994, 86, 243; A. M. Al-Ajlouni and J. H. Espenson, J. Am. Chem. Soc., 1995, 117, 9243; O. Pestovsky, R. van Eldik, P. Huston and J. H. Espenson, J. Chem. Soc., Dalton Trans. 2, 1995, 133; W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149; W. Adam and C. M. Mitchell, Angew. Chem., Int. Ed. Engl., 1996, 35, 533; T. R. Boelow and C. S. Spilling, Tetrahedron Lett., 1996, 37, 2717; A. M. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 1996, 61, 3969; W. A. Herrmann, J. D. G. Correia, M. U. Rauch, G. R. J. Artus and F. E. Kühn, J. Mol. Cat., 1997, 118, 33; ARCO Chemical Technology (G. L. Crocco, W. P. Shum, J. G. Zajacek and H. S. Kesling, Jr.) US 5,166,372, 1992;
14. (b) For MTO-catalysed epoxidation of alkenes, see Hoechst AG (W. A. Herrmann, D. W. Marz, J. G. Kuchler, G. Weichselbaumer and R. W. Fischer) DE 3,902,357, 1989; W. A. Herrmann, R. W. Fischer and D. W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; W. A. Herrmann, R. W. Fischer, M. U. Rauch and W. Scherer, J. Mol. Catal., 1994, 86, 243; A. M. Al-Ajlouni and J. H. Espenson, J. Am. Chem. Soc., 1995, 117, 9243; O. Pestovsky, R. van Eldik, P. Huston and J. H. Espenson, J. Chem. Soc., Dalton Trans. 2, 1995, 133; W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149; W. Adam and C. M. Mitchell, Angew. Chem., Int. Ed. Engl., 1996, 35, 533; T. R. Boelow and C. S. Spilling, Tetrahedron Lett., 1996, 37, 2717; A. M. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 1996, 61, 3969; W. A. Herrmann, J. D. G. Correia, M. U. Rauch, G. R. J. Artus and F. E. Kühn, J. Mol. Cat., 1997, 118, 33; ARCO Chemical Technology (G. L. Crocco, W. P. Shum, J. G. Zajacek and H. S. Kesling, Jr.) US 5,166,372, 1992;
15. (b) For MTO-catalysed epoxidation of alkenes, see Hoechst AG (W. A. Herrmann, D. W. Marz, J. G. Kuchler, G. Weichselbaumer and R. W. Fischer) DE 3,902,357, 1989; W. A. Herrmann, R. W. Fischer and D. W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; W. A. Herrmann, R. W. Fischer, M. U. Rauch and W. Scherer, J. Mol. Catal., 1994, 86, 243; A. M. Al-Ajlouni and J. H. Espenson, J. Am. Chem. Soc., 1995, 117, 9243; O. Pestovsky, R. van Eldik, P. Huston and J. H. Espenson, J. Chem. Soc., Dalton Trans. 2, 1995, 133; W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149; W. Adam and C. M. Mitchell, Angew. Chem., Int. Ed. Engl., 1996, 35, 533; T. R. Boelow and C. S. Spilling, Tetrahedron Lett., 1996, 37, 2717; A. M. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 1996, 61, 3969; W. A. Herrmann, J. D. G. Correia, M. U. Rauch, G. R. J. Artus and F. E. Kühn, J. Mol. Cat., 1997, 118, 33; ARCO Chemical Technology (G. L. Crocco, W. P. Shum, J. G. Zajacek and H. S. Kesling, Jr.) US 5,166,372, 1992;
16. (b) For MTO-catalysed epoxidation of alkenes, see Hoechst AG (W. A. Herrmann, D. W. Marz, J. G. Kuchler, G. Weichselbaumer and R. W. Fischer) DE 3,902,357, 1989; W. A. Herrmann, R. W. Fischer and D. W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; W. A. Herrmann, R. W. Fischer, M. U. Rauch and W. Scherer, J. Mol. Catal., 1994, 86, 243; A. M. Al-Ajlouni and J. H. Espenson, J. Am. Chem. Soc., 1995, 117, 9243; O. Pestovsky, R. van Eldik, P. Huston and J. H. Espenson, J. Chem. Soc., Dalton Trans. 2, 1995, 133; W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149; W. Adam and C. M. Mitchell, Angew. Chem., Int. Ed. Engl., 1996, 35, 533; T. R. Boelow and C. S. Spilling, Tetrahedron Lett., 1996, 37, 2717; A. M. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 1996, 61, 3969; W. A. Herrmann, J. D. G. Correia, M. U. Rauch, G. R. J. Artus and F. E. Kühn, J. Mol. Cat., 1997, 118, 33; ARCO Chemical Technology (G. L. Crocco, W. P. Shum, J. G. Zajacek and H. S. Kesling, Jr.) US 5,166,372, 1992;
17. (b) For MTO-catalysed epoxidation of alkenes, see Hoechst AG (W. A. Herrmann, D. W. Marz, J. G. Kuchler, G. Weichselbaumer and R. W. Fischer) DE 3,902,357, 1989; W. A. Herrmann, R. W. Fischer and D. W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; W. A. Herrmann, R. W. Fischer, M. U. Rauch and W. Scherer, J. Mol. Catal., 1994, 86, 243; A. M. Al-Ajlouni and J. H. Espenson, J. Am. Chem. Soc., 1995, 117, 9243; O. Pestovsky, R. van Eldik, P. Huston and J. H. Espenson, J. Chem. Soc., Dalton Trans. 2, 1995, 133; W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149; W. Adam and C. M. Mitchell, Angew. Chem., Int. Ed. Engl., 1996, 35, 533; T. R. Boelow and C. S. Spilling, Tetrahedron Lett., 1996, 37, 2717; A. M. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 1996, 61, 3969; W. A. Herrmann, J. D. G. Correia, M. U. Rauch, G. R. J. Artus and F. E. Kühn, J. Mol. Cat., 1997, 118, 33; ARCO Chemical Technology (G. L. Crocco, W. P. Shum, J. G. Zajacek and H. S. Kesling, Jr.) US 5,166,372, 1992;
18. (b) For MTO-catalysed epoxidation of alkenes, see Hoechst AG (W. A. Herrmann, D. W. Marz, J. G. Kuchler, G. Weichselbaumer and R. W. Fischer) DE 3,902,357, 1989; W. A. Herrmann, R. W. Fischer and D. W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; W. A. Herrmann, R. W. Fischer, M. U. Rauch and W. Scherer, J. Mol. Catal., 1994, 86, 243; A. M. Al-Ajlouni and J. H. Espenson, J. Am. Chem. Soc., 1995, 117, 9243; O. Pestovsky, R. van Eldik, P. Huston and J. H. Espenson, J. Chem. Soc., Dalton Trans. 2, 1995, 133; W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149; W. Adam and C. M. Mitchell, Angew. Chem., Int. Ed. Engl., 1996, 35, 533; T. R. Boelow and C. S. Spilling, Tetrahedron Lett., 1996, 37, 2717; A. M. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 1996, 61, 3969; W. A. Herrmann, J. D. G. Correia, M. U. Rauch, G. R. J. Artus and F. E. Kühn, J. Mol. Cat., 1997, 118, 33; ARCO Chemical Technology (G. L. Crocco, W. P. Shum, J. G. Zajacek and H. S. Kesling, Jr.) US 5,166,372, 1992;
19. (b) For MTO-catalysed epoxidation of alkenes, see Hoechst AG (W. A. Herrmann, D. W. Marz, J. G. Kuchler, G. Weichselbaumer and R. W. Fischer) DE 3,902,357, 1989; W. A. Herrmann, R. W. Fischer and D. W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; W. A. Herrmann, R. W. Fischer, M. U. Rauch and W. Scherer, J. Mol. Catal., 1994, 86, 243; A. M. Al-Ajlouni and J. H. Espenson, J. Am. Chem. Soc., 1995, 117, 9243; O. Pestovsky, R. van Eldik, P. Huston and J. H. Espenson, J. Chem. Soc., Dalton Trans. 2, 1995, 133; W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149; W. Adam and C. M. Mitchell, Angew. Chem., Int. Ed. Engl., 1996, 35, 533; T. R. Boelow and C. S. Spilling, Tetrahedron Lett., 1996, 37, 2717; A. M. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 1996, 61, 3969; W. A. Herrmann, J. D. G. Correia, M. U. Rauch, G. R. J. Artus and F. E. Kühn, J. Mol. Cat., 1997, 118, 33; ARCO Chemical Technology (G. L. Crocco, W. P. Shum, J. G. Zajacek and H. S. Kesling, Jr.) US 5,166,372, 1992;
20. (b) For MTO-catalysed epoxidation of alkenes, see Hoechst AG (W. A. Herrmann, D. W. Marz, J. G. Kuchler, G. Weichselbaumer and R. W. Fischer) DE 3,902,357, 1989; W. A. Herrmann, R. W. Fischer and D. W. Marz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1638; W. A. Herrmann, R. W. Fischer, M. U. Rauch and W. Scherer, J. Mol. Catal., 1994, 86, 243; A. M. Al-Ajlouni and J. H. Espenson, J. Am. Chem. Soc., 1995, 117, 9243; O. Pestovsky, R. van Eldik, P. Huston and J. H. Espenson, J. Chem. Soc., Dalton Trans. 2, 1995, 133; W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149; W. Adam and C. M. Mitchell, Angew. Chem., Int. Ed. Engl., 1996, 35, 533; T. R. Boelow and C. S. Spilling, Tetrahedron Lett., 1996, 37, 2717; A. M. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 1996, 61, 3969; W. A. Herrmann, J. D. G. Correia, M. U. Rauch, G. R. J. Artus and F. E. Kühn, J. Mol. Cat., 1997, 118, 33; ARCO Chemical Technology (G. L. Crocco, W. P. Shum, J. G. Zajacek and H. S. Kesling, Jr.) US 5,166,372, 1992;
21. (c) For reviews on epoxidation of alkenes, see G. Strukul, In Catalytic Oxidation with Hydrogen Peroxide as Oxidant, Kluwer, Dordrecht, 1992; R. A. Sheldon, In Applied Homogeneous Catalysis with Organometallic Compounds, ed. B. Cornils and W. A. Herrmann, VCH, Weinheim, 1996.
22. (c) For reviews on epoxidation of alkenes, see G. Strukul, In Catalytic Oxidation with Hydrogen Peroxide as Oxidant, Kluwer, Dordrecht, 1992; R. A. Sheldon, In Applied Homogeneous Catalysis with Organometallic Compounds, ed. B. Cornils and W. A. Herrmann, VCH, Weinheim, 1996.
23. D. J. Berrisford, C. Bolm and K. B. Sharpless, Angew. Chem., Int. Ed. Engl., 1995, 34, 1059.
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