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Volumn 59, Issue 37, 2003, Pages 7403-7408

Selective epoxidation of monoterpenes with H2O2 and polymer-supported methylrheniumtrioxide systems

Author keywords

Epoxidation; Terpenic epoxides; pinene oxide

Indexed keywords

4 VINYLPYRIDINE; HYDROGEN PEROXIDE; METHYLRHENIUM TRIOXIDE; METHYLRHENIUMTRIOXIDE; OXIDE; OXIDIZING AGENT; POLYMER; PYRIDINE DERIVATIVE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0042883849     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01145-1     Document Type: Article
Times cited : (57)

References (45)
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    • See for example: (a) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (b) Gisdakis P., Antonczak S., Köstlmeier S., Herrmann W.A., Rösch N. Angew. Chem., Int. Ed. Engl. 37:1998;2211 (c) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (d) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (e) Herrmann W.A., Fischer R.W., Rauch M.U., Scherer W. J. Mol. Catal. 86:1994;243-266 (f) Copèret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (g) Ferreira P., Xue W.-M.-., Bencze E., Herdtweck E., Kühn F.E. Inorg. Chem. 40:2001;5834-5841 (h) Herrmann W.A., Fischer R.W., Scherer W., Rauch M.U. Angew. Chem., Int. Ed. Engl. 32:1993;1157-1160. For recent computational studies on MTO epoxidation see: (i) Gisdakis P., Yudanov I.V., Rösch N. Inorg. Chem. 40:2001;3755-3765 (j) Di Valentin C., Gandolfi R., Gisdakis P., Rösch N. J. Am. Chem. Soc. 123:2001;2365-2376.
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    • 0002001751 scopus 로고    scopus 로고
    • See for example: (a) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (b) Gisdakis P., Antonczak S., Köstlmeier S., Herrmann W.A., Rösch N. Angew. Chem., Int. Ed. Engl. 37:1998;2211 (c) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (d) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (e) Herrmann W.A., Fischer R.W., Rauch M.U., Scherer W. J. Mol. Catal. 86:1994;243-266 (f) Copèret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (g) Ferreira P., Xue W.-M.-., Bencze E., Herdtweck E., Kühn F.E. Inorg. Chem. 40:2001;5834-5841 (h) Herrmann W.A., Fischer R.W., Scherer W., Rauch M.U. Angew. Chem., Int. Ed. Engl. 32:1993;1157-1160. For recent computational studies on MTO epoxidation see: (i) Gisdakis P., Yudanov I.V., Rösch N. Inorg. Chem. 40:2001;3755-3765 (j) Di Valentin C., Gandolfi R., Gisdakis P., Rösch N. J. Am. Chem. Soc. 123:2001;2365-2376.
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    • 0035813249 scopus 로고    scopus 로고
    • See for example: (a) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (b) Gisdakis P., Antonczak S., Köstlmeier S., Herrmann W.A., Rösch N. Angew. Chem., Int. Ed. Engl. 37:1998;2211 (c) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (d) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (e) Herrmann W.A., Fischer R.W., Rauch M.U., Scherer W. J. Mol. Catal. 86:1994;243-266 (f) Copèret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (g) Ferreira P., Xue W.-M.-., Bencze E., Herdtweck E., Kühn F.E. Inorg. Chem. 40:2001;5834-5841 (h) Herrmann W.A., Fischer R.W., Scherer W., Rauch M.U. Angew. Chem., Int. Ed. Engl. 32:1993;1157-1160. For recent computational studies on MTO epoxidation see: (i) Gisdakis P., Yudanov I.V., Rösch N. Inorg. Chem. 40:2001;3755-3765 (j) Di Valentin C., Gandolfi R., Gisdakis P., Rösch N. J. Am. Chem. Soc. 123:2001;2365-2376.
    • (2001) Inorg. Chem. , vol.40 , pp. 5834-5841
    • Ferreira, P.1    Xue, W.-M.-.2    Bencze, E.3    Herdtweck, E.4    Kühn, F.E.5
  • 22
    • 33748224009 scopus 로고
    • See for example: (a) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (b) Gisdakis P., Antonczak S., Köstlmeier S., Herrmann W.A., Rösch N. Angew. Chem., Int. Ed. Engl. 37:1998;2211 (c) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (d) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (e) Herrmann W.A., Fischer R.W., Rauch M.U., Scherer W. J. Mol. Catal. 86:1994;243-266 (f) Copèret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (g) Ferreira P., Xue W.-M.-., Bencze E., Herdtweck E., Kühn F.E. Inorg. Chem. 40:2001;5834-5841 (h) Herrmann W.A., Fischer R.W., Scherer W., Rauch M.U. Angew. Chem., Int. Ed. Engl. 32:1993;1157-1160. For recent computational studies on MTO epoxidation see: (i) Gisdakis P., Yudanov I.V., Rösch N. Inorg. Chem. 40:2001;3755-3765 (j) Di Valentin C., Gandolfi R., Gisdakis P., Rösch N. J. Am. Chem. Soc. 123:2001;2365-2376.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 1157-1160
    • Herrmann, W.A.1    Fischer, R.W.2    Scherer, W.3    Rauch, M.U.4
  • 23
    • 0035898079 scopus 로고    scopus 로고
    • See for example: (a) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (b) Gisdakis P., Antonczak S., Köstlmeier S., Herrmann W.A., Rösch N. Angew. Chem., Int. Ed. Engl. 37:1998;2211 (c) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (d) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (e) Herrmann W.A., Fischer R.W., Rauch M.U., Scherer W. J. Mol. Catal. 86:1994;243-266 (f) Copèret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (g) Ferreira P., Xue W.-M.-., Bencze E., Herdtweck E., Kühn F.E. Inorg. Chem. 40:2001;5834-5841 (h) Herrmann W.A., Fischer R.W., Scherer W., Rauch M.U. Angew. Chem., Int. Ed. Engl. 32:1993;1157-1160. For recent computational studies on MTO epoxidation see: (i) Gisdakis P., Yudanov I.V., Rösch N. Inorg. Chem. 40:2001;3755-3765 (j) Di Valentin C., Gandolfi R., Gisdakis P., Rösch N. J. Am. Chem. Soc. 123:2001;2365-2376.
    • (2001) Inorg. Chem. , vol.40 , pp. 3755-3765
    • Gisdakis, P.1    Yudanov, I.V.2    Rösch, N.3
  • 24
    • 0034807115 scopus 로고    scopus 로고
    • See for example: (a). For recent computational studies on MTO epoxidation see: (i)
    • See for example: (a) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (b) Gisdakis P., Antonczak S., Köstlmeier S., Herrmann W.A., Rösch N. Angew. Chem., Int. Ed. Engl. 37:1998;2211 (c) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (d) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (e) Herrmann W.A., Fischer R.W., Rauch M.U., Scherer W. J. Mol. Catal. 86:1994;243-266 (f) Copèret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (g) Ferreira P., Xue W.-M.-., Bencze E., Herdtweck E., Kühn F.E. Inorg. Chem. 40:2001;5834-5841 (h) Herrmann W.A., Fischer R.W., Scherer W., Rauch M.U. Angew. Chem., Int. Ed. Engl. 32:1993;1157-1160. For recent computational studies on MTO epoxidation see: (i) Gisdakis P., Yudanov I.V., Rösch N. Inorg. Chem. 40:2001;3755-3765 (j) Di Valentin C., Gandolfi R., Gisdakis P., Rösch N. J. Am. Chem. Soc. 123:2001;2365-2376.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 2365-2376
    • Di Valentin, C.1    Gandolfi, R.2    Gisdakis, P.3    Rösch, N.4
  • 37
    • 85031078276 scopus 로고    scopus 로고
    • 2-4 behave in a similar way
    • Catalysts 2-4 behave in a similar way.
  • 44
    • 85031067324 scopus 로고    scopus 로고
    • Beil. 5, 152. The product was identical to an authentic commercially sample (Aldrich, Co.)
    • Beil. 5, 152. The product was identical to an authentic commercially sample (Aldrich, Co.)
  • 45
    • 85031084830 scopus 로고    scopus 로고
    • Beil. 17, 44. The product was identical to an authentic commercially sample (Aldrich, Co.)
    • Beil. 17, 44. The product was identical to an authentic commercially sample (Aldrich, Co.).


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