Trichloroisocyanuric acid: A convenient oxidation reagent for phase-transfer catalytic epoxidation of enones under non-aqueous conditions

Advanced Synthesis and Catalysis

Volumn 346, Issue 6, 2004, Pages 691-696

  Ye, Jinxing ^a   Wang, Yongcan ^a   Chen, Jiping ^a   Liang, Xinmiao ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Enones; Epoxidation; Organic catalysis; Phase tranfer catalysis; Trichloroisocyanuric acid

Indexed keywords

BROMINE DERIVATIVE; CHALCONE DERIVATIVE; CYANURIC ACID; EPOXIDE; HYDROGEN PEROXIDE; HYPOCHLORITE;

AQUEOUS SOLUTION; ARTICLE; CATALYST; EPOXIDATION; OXIDATION KINETICS; PHASE TRANSITION;

EID: 3042708198     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303227     Document Type: Article

References (49)

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31. For a recent review on the use of trichloroisocyanuric acid, see: U. Tilstam, H. Weinmann, Org. Process Res. Dev. 2002, 4, 384; for selected examples on the use of trichloroisocyanuric acid, see: a) E. C. Juenge, D. A. Beal, Tetrahedron Lett. 1968, 5819; b) T. Cohen, Z. Kosarych, K. Suzuki, L.-C. Yu, J. Org. Chem. 1985, 50, 2965; c) T. R. Walters, W. W. Zajac Jr., J. M. Woods, J. Org. Chem. 1991, 56, 316; d) G. A. Hiegel, M. Nalbandy, Synth. Commun. 1992, 22, 1589; e) U. Tilstam, M. Harre, T. Heckrodt, H. Weinmann, Tetrahedron Lett. 2001, 42, 5385; f) L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett. 2001, 3, 3041; g) L. De Luca, G. Giacomelli, M. Simonetta, A. Porcheddu, J. Org. Chem. 2003, 68, 4999; h) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Synlett 2001, 1641; i) M. A. Zolfigol, A. G. Choghamarani, H. Hazarkhani, Synlett 2002, 1002; j) M. A. Zolfigol, E. Ghaemi, E. Madrakian, Synlett 2003, 191; k) M. Wengert, A. M. Sanseverino, M. C. S. de Mattos, J. Braz. Chem. Soc. 2002, 13, 700; l) G. F. Mendonca, A. M. Sanseverino, M. C. S. de Mattos, Synthesis 2003, 45.
32. For a recent review on the use of trichloroisocyanuric acid, see: U. Tilstam, H. Weinmann, Org. Process Res. Dev. 2002, 4, 384; for selected examples on the use of trichloroisocyanuric acid, see: a) E. C. Juenge, D. A. Beal, Tetrahedron Lett. 1968, 5819; b) T. Cohen, Z. Kosarych, K. Suzuki, L.-C. Yu, J. Org. Chem. 1985, 50, 2965; c) T. R. Walters, W. W. Zajac Jr., J. M. Woods, J. Org. Chem. 1991, 56, 316; d) G. A. Hiegel, M. Nalbandy, Synth. Commun. 1992, 22, 1589; e) U. Tilstam, M. Harre, T. Heckrodt, H. Weinmann, Tetrahedron Lett. 2001, 42, 5385; f) L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett. 2001, 3, 3041; g) L. De Luca, G. Giacomelli, M. Simonetta, A. Porcheddu, J. Org. Chem. 2003, 68, 4999; h) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Synlett 2001, 1641; i) M. A. Zolfigol, A. G. Choghamarani, H. Hazarkhani, Synlett 2002, 1002; j) M. A. Zolfigol, E. Ghaemi, E. Madrakian, Synlett 2003, 191; k) M. Wengert, A. M. Sanseverino, M. C. S. de Mattos, J. Braz. Chem. Soc. 2002, 13, 700; l) G. F. Mendonca, A. M. Sanseverino, M. C. S. de Mattos, Synthesis 2003, 45.
33. For a recent review on the use of trichloroisocyanuric acid, see: U. Tilstam, H. Weinmann, Org. Process Res. Dev. 2002, 4, 384; for selected examples on the use of trichloroisocyanuric acid, see: a) E. C. Juenge, D. A. Beal, Tetrahedron Lett. 1968, 5819; b) T. Cohen, Z. Kosarych, K. Suzuki, L.-C. Yu, J. Org. Chem. 1985, 50, 2965; c) T. R. Walters, W. W. Zajac Jr., J. M. Woods, J. Org. Chem. 1991, 56, 316; d) G. A. Hiegel, M. Nalbandy, Synth. Commun. 1992, 22, 1589; e) U. Tilstam, M. Harre, T. Heckrodt, H. Weinmann, Tetrahedron Lett. 2001, 42, 5385; f) L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett. 2001, 3, 3041; g) L. De Luca, G. Giacomelli, M. Simonetta, A. Porcheddu, J. Org. Chem. 2003, 68, 4999; h) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Synlett 2001, 1641; i) M. A. Zolfigol, A. G. Choghamarani, H. Hazarkhani, Synlett 2002, 1002; j) M. A. Zolfigol, E. Ghaemi, E. Madrakian, Synlett 2003, 191; k) M. Wengert, A. M. Sanseverino, M. C. S. de Mattos, J. Braz. Chem. Soc. 2002, 13, 700; l) G. F. Mendonca, A. M. Sanseverino, M. C. S. de Mattos, Synthesis 2003, 45.
34. For a recent review on the use of trichloroisocyanuric acid, see: U. Tilstam, H. Weinmann, Org. Process Res. Dev. 2002, 4, 384; for selected examples on the use of trichloroisocyanuric acid, see: a) E. C. Juenge, D. A. Beal, Tetrahedron Lett. 1968, 5819; b) T. Cohen, Z. Kosarych, K. Suzuki, L.-C. Yu, J. Org. Chem. 1985, 50, 2965; c) T. R. Walters, W. W. Zajac Jr., J. M. Woods, J. Org. Chem. 1991, 56, 316; d) G. A. Hiegel, M. Nalbandy, Synth. Commun. 1992, 22, 1589; e) U. Tilstam, M. Harre, T. Heckrodt, H. Weinmann, Tetrahedron Lett. 2001, 42, 5385; f) L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett. 2001, 3, 3041; g) L. De Luca, G. Giacomelli, M. Simonetta, A. Porcheddu, J. Org. Chem. 2003, 68, 4999; h) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Synlett 2001, 1641; i) M. A. Zolfigol, A. G. Choghamarani, H. Hazarkhani, Synlett 2002, 1002; j) M. A. Zolfigol, E. Ghaemi, E. Madrakian, Synlett 2003, 191; k) M. Wengert, A. M. Sanseverino, M. C. S. de Mattos, J. Braz. Chem. Soc. 2002, 13, 700; l) G. F. Mendonca, A. M. Sanseverino, M. C. S. de Mattos, Synthesis 2003, 45.
35. For a recent review on the use of trichloroisocyanuric acid, see: U. Tilstam, H. Weinmann, Org. Process Res. Dev. 2002, 4, 384; for selected examples on the use of trichloroisocyanuric acid, see: a) E. C. Juenge, D. A. Beal, Tetrahedron Lett. 1968, 5819; b) T. Cohen, Z. Kosarych, K. Suzuki, L.-C. Yu, J. Org. Chem. 1985, 50, 2965; c) T. R. Walters, W. W. Zajac Jr., J. M. Woods, J. Org. Chem. 1991, 56, 316; d) G. A. Hiegel, M. Nalbandy, Synth. Commun. 1992, 22, 1589; e) U. Tilstam, M. Harre, T. Heckrodt, H. Weinmann, Tetrahedron Lett. 2001, 42, 5385; f) L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett. 2001, 3, 3041; g) L. De Luca, G. Giacomelli, M. Simonetta, A. Porcheddu, J. Org. Chem. 2003, 68, 4999; h) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Synlett 2001, 1641; i) M. A. Zolfigol, A. G. Choghamarani, H. Hazarkhani, Synlett 2002, 1002; j) M. A. Zolfigol, E. Ghaemi, E. Madrakian, Synlett 2003, 191; k) M. Wengert, A. M. Sanseverino, M. C. S. de Mattos, J. Braz. Chem. Soc. 2002, 13, 700; l) G. F. Mendonca, A. M. Sanseverino, M. C. S. de Mattos, Synthesis 2003, 45.
36. For a recent review on the use of trichloroisocyanuric acid, see: U. Tilstam, H. Weinmann, Org. Process Res. Dev. 2002, 4, 384; for selected examples on the use of trichloroisocyanuric acid, see: a) E. C. Juenge, D. A. Beal, Tetrahedron Lett. 1968, 5819; b) T. Cohen, Z. Kosarych, K. Suzuki, L.-C. Yu, J. Org. Chem. 1985, 50, 2965; c) T. R. Walters, W. W. Zajac Jr., J. M. Woods, J. Org. Chem. 1991, 56, 316; d) G. A. Hiegel, M. Nalbandy, Synth. Commun. 1992, 22, 1589; e) U. Tilstam, M. Harre, T. Heckrodt, H. Weinmann, Tetrahedron Lett. 2001, 42, 5385; f) L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett. 2001, 3, 3041; g) L. De Luca, G. Giacomelli, M. Simonetta, A. Porcheddu, J. Org. Chem. 2003, 68, 4999; h) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Synlett 2001, 1641; i) M. A. Zolfigol, A. G. Choghamarani, H. Hazarkhani, Synlett 2002, 1002; j) M. A. Zolfigol, E. Ghaemi, E. Madrakian, Synlett 2003, 191; k) M. Wengert, A. M. Sanseverino, M. C. S. de Mattos, J. Braz. Chem. Soc. 2002, 13, 700; l) G. F. Mendonca, A. M. Sanseverino, M. C. S. de Mattos, Synthesis 2003, 45.
37. For a recent review on the use of trichloroisocyanuric acid, see: U. Tilstam, H. Weinmann, Org. Process Res. Dev. 2002, 4, 384; for selected examples on the use of trichloroisocyanuric acid, see: a) E. C. Juenge, D. A. Beal, Tetrahedron Lett. 1968, 5819; b) T. Cohen, Z. Kosarych, K. Suzuki, L.-C. Yu, J. Org. Chem. 1985, 50, 2965; c) T. R. Walters, W. W. Zajac Jr., J. M. Woods, J. Org. Chem. 1991, 56, 316; d) G. A. Hiegel, M. Nalbandy, Synth. Commun. 1992, 22, 1589; e) U. Tilstam, M. Harre, T. Heckrodt, H. Weinmann, Tetrahedron Lett. 2001, 42, 5385; f) L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett. 2001, 3, 3041; g) L. De Luca, G. Giacomelli, M. Simonetta, A. Porcheddu, J. Org. Chem. 2003, 68, 4999; h) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Synlett 2001, 1641; i) M. A. Zolfigol, A. G. Choghamarani, H. Hazarkhani, Synlett 2002, 1002; j) M. A. Zolfigol, E. Ghaemi, E. Madrakian, Synlett 2003, 191; k) M. Wengert, A. M. Sanseverino, M. C. S. de Mattos, J. Braz. Chem. Soc. 2002, 13, 700; l) G. F. Mendonca, A. M. Sanseverino, M. C. S. de Mattos, Synthesis 2003, 45.
38. For a recent review on the use of trichloroisocyanuric acid, see: U. Tilstam, H. Weinmann, Org. Process Res. Dev. 2002, 4, 384; for selected examples on the use of trichloroisocyanuric acid, see: a) E. C. Juenge, D. A. Beal, Tetrahedron Lett. 1968, 5819; b) T. Cohen, Z. Kosarych, K. Suzuki, L.-C. Yu, J. Org. Chem. 1985, 50, 2965; c) T. R. Walters, W. W. Zajac Jr., J. M. Woods, J. Org. Chem. 1991, 56, 316; d) G. A. Hiegel, M. Nalbandy, Synth. Commun. 1992, 22, 1589; e) U. Tilstam, M. Harre, T. Heckrodt, H. Weinmann, Tetrahedron Lett. 2001, 42, 5385; f) L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett. 2001, 3, 3041; g) L. De Luca, G. Giacomelli, M. Simonetta, A. Porcheddu, J. Org. Chem. 2003, 68, 4999; h) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Synlett 2001, 1641; i) M. A. Zolfigol, A. G. Choghamarani, H. Hazarkhani, Synlett 2002, 1002; j) M. A. Zolfigol, E. Ghaemi, E. Madrakian, Synlett 2003, 191; k) M. Wengert, A. M. Sanseverino, M. C. S. de Mattos, J. Braz. Chem. Soc. 2002, 13, 700; l) G. F. Mendonca, A. M. Sanseverino, M. C. S. de Mattos, Synthesis 2003, 45.
39. For a recent review on the use of trichloroisocyanuric acid, see: U. Tilstam, H. Weinmann, Org. Process Res. Dev. 2002, 4, 384; for selected examples on the use of trichloroisocyanuric acid, see: a) E. C. Juenge, D. A. Beal, Tetrahedron Lett. 1968, 5819; b) T. Cohen, Z. Kosarych, K. Suzuki, L.-C. Yu, J. Org. Chem. 1985, 50, 2965; c) T. R. Walters, W. W. Zajac Jr., J. M. Woods, J. Org. Chem. 1991, 56, 316; d) G. A. Hiegel, M. Nalbandy, Synth. Commun. 1992, 22, 1589; e) U. Tilstam, M. Harre, T. Heckrodt, H. Weinmann, Tetrahedron Lett. 2001, 42, 5385; f) L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett. 2001, 3, 3041; g) L. De Luca, G. Giacomelli, M. Simonetta, A. Porcheddu, J. Org. Chem. 2003, 68, 4999; h) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Synlett 2001, 1641; i) M. A. Zolfigol, A. G. Choghamarani, H. Hazarkhani, Synlett 2002, 1002; j) M. A. Zolfigol, E. Ghaemi, E. Madrakian, Synlett 2003, 191; k) M. Wengert, A. M. Sanseverino, M. C. S. de Mattos, J. Braz. Chem. Soc. 2002, 13, 700; l) G. F. Mendonca, A. M. Sanseverino, M. C. S. de Mattos, Synthesis 2003, 45.
40. For a recent review on the use of trichloroisocyanuric acid, see: U. Tilstam, H. Weinmann, Org. Process Res. Dev. 2002, 4, 384; for selected examples on the use of trichloroisocyanuric acid, see: a) E. C. Juenge, D. A. Beal, Tetrahedron Lett. 1968, 5819; b) T. Cohen, Z. Kosarych, K. Suzuki, L.-C. Yu, J. Org. Chem. 1985, 50, 2965; c) T. R. Walters, W. W. Zajac Jr., J. M. Woods, J. Org. Chem. 1991, 56, 316; d) G. A. Hiegel, M. Nalbandy, Synth. Commun. 1992, 22, 1589; e) U. Tilstam, M. Harre, T. Heckrodt, H. Weinmann, Tetrahedron Lett. 2001, 42, 5385; f) L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett. 2001, 3, 3041; g) L. De Luca, G. Giacomelli, M. Simonetta, A. Porcheddu, J. Org. Chem. 2003, 68, 4999; h) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Synlett 2001, 1641; i) M. A. Zolfigol, A. G. Choghamarani, H. Hazarkhani, Synlett 2002, 1002; j) M. A. Zolfigol, E. Ghaemi, E. Madrakian, Synlett 2003, 191; k) M. Wengert, A. M. Sanseverino, M. C. S. de Mattos, J. Braz. Chem. Soc. 2002, 13, 700; l) G. F. Mendonca, A. M. Sanseverino, M. C. S. de Mattos, Synthesis 2003, 45.
41. For a recent review on the use of trichloroisocyanuric acid, see: U. Tilstam, H. Weinmann, Org. Process Res. Dev. 2002, 4, 384; for selected examples on the use of trichloroisocyanuric acid, see: a) E. C. Juenge, D. A. Beal, Tetrahedron Lett. 1968, 5819; b) T. Cohen, Z. Kosarych, K. Suzuki, L.-C. Yu, J. Org. Chem. 1985, 50, 2965; c) T. R. Walters, W. W. Zajac Jr., J. M. Woods, J. Org. Chem. 1991, 56, 316; d) G. A. Hiegel, M. Nalbandy, Synth. Commun. 1992, 22, 1589; e) U. Tilstam, M. Harre, T. Heckrodt, H. Weinmann, Tetrahedron Lett. 2001, 42, 5385; f) L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett. 2001, 3, 3041; g) L. De Luca, G. Giacomelli, M. Simonetta, A. Porcheddu, J. Org. Chem. 2003, 68, 4999; h) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Synlett 2001, 1641; i) M. A. Zolfigol, A. G. Choghamarani, H. Hazarkhani, Synlett 2002, 1002; j) M. A. Zolfigol, E. Ghaemi, E. Madrakian, Synlett 2003, 191; k) M. Wengert, A. M. Sanseverino, M. C. S. de Mattos, J. Braz. Chem. Soc. 2002, 13, 700; l) G. F. Mendonca, A. M. Sanseverino, M. C. S. de Mattos, Synthesis 2003, 45.
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