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For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references therein.
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For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references therein.
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For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references therein.
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For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references therein.
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For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references therein.
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For examples of asymmetric epoxidation mediated by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. See ref 2g. Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921-2926.
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For examples of asymmetric epoxidation mediated by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. See ref 2g. Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921-2926.
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For examples of asymmetric epoxidation mediated by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. See ref 2g. Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921-2926.
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For examples of asymmetric epoxidation mediated by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. See ref 2g. Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587-3606. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921-2926.
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-
For the leading references on the epoxidation of hydroxyalkenes by dioxiranes, see: (a) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (b) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437-2440. Adam, W.; Smerz, A. K. Tetrahedron 1995, 51, 13039-13044. Adam, W.; Smerz, A. K. J. Org. Chem. 1995, 61, 3506-3510. (e) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841. (f) See ref 1d. (g) Adam, W.; Mitchell, C. M.; Paredes, R.; Smerz, A. K. Veloza, A. Liebigs Ann./Rec. 1997, 1365-1369.
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Murray, R.W.1
Singh, M.2
Williams, B.L.3
Moncrieff, H.M.4
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27
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85034462665
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See ref 1d
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For the leading references on the epoxidation of hydroxyalkenes by dioxiranes, see: (a) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (b) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437-2440. Adam, W.; Smerz, A. K. Tetrahedron 1995, 51, 13039-13044. Adam, W.; Smerz, A. K. J. Org. Chem. 1995, 61, 3506-3510. (e) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841. (f) See ref 1d. (g) Adam, W.; Mitchell, C. M.; Paredes, R.; Smerz, A. K. Veloza, A. Liebigs Ann./Rec. 1997, 1365-1369.
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28
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0003727060
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For the leading references on the epoxidation of hydroxyalkenes by dioxiranes, see: (a) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (b) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. Tetrahedron Lett. 1995, 36, 2437-2440. Adam, W.; Smerz, A. K. Tetrahedron 1995, 51, 13039-13044. Adam, W.; Smerz, A. K. J. Org. Chem. 1995, 61, 3506-3510. (e) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841. (f) See ref 1d. (g) Adam, W.; Mitchell, C. M.; Paredes, R.; Smerz, A. K. Veloza, A. Liebigs Ann./Rec. 1997, 1365-1369.
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Liebigs Ann./Rec.
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Adam, W.1
Mitchell, C.M.2
Paredes, R.3
Smerz, A.K.4
Veloza, A.5
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29
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85034484749
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It should be noted that dioxirane 2 was very short-lived. It has been extremely difficult to isolate this species. In this case, it was hoped that some dioxirane would remain within a short time
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It should be noted that dioxirane 2 was very short-lived. It has been extremely difficult to isolate this species. In this case, it was hoped that some dioxirane would remain within a short time.
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30
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0001014759
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For the leading references on the epoxidation of olefins by Oxone, see: (a) Bloch, R.; Abecassis, J.; Hassan, D. J. Org. Chem. 1985, 50, 1544-1545. (b) Zhu, W.; Ford, W. T. J. Org. Chem. 1991, 56, 7022-7026. (c) See ref 5g.
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Hassan, D.3
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31
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0001349563
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For the leading references on the epoxidation of olefins by Oxone, see: (a) Bloch, R.; Abecassis, J.; Hassan, D. J. Org. Chem. 1985, 50, 1544-1545. (b) Zhu, W.; Ford, W. T. J. Org. Chem. 1991, 56, 7022-7026. (c) See ref 5g.
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Ford, W.T.2
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0001014759
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See ref 5g
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For the leading references on the epoxidation of olefins by Oxone, see: (a) Bloch, R.; Abecassis, J.; Hassan, D. J. Org. Chem. 1985, 50, 1544-1545. (b) Zhu, W.; Ford, W. T. J. Org. Chem. 1991, 56, 7022-7026. (c) See ref 5g.
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33
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85034464049
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Such hydrogen bonding is likely to enhance the epoxidation reactivity of Oxone by dispersing the negative charge of Oxone (see ref 5g)
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Such hydrogen bonding is likely to enhance the epoxidation reactivity of Oxone by dispersing the negative charge of Oxone (see ref 5g).
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34
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0003544583
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Ojima, I., Ed.; VCH: New York, Chapter 4.1
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For highly enantioselective epoxidation of allylic alcohols, see: (a) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.1. (b) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1-299.
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