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Volumn 44, Issue 10, 2003, Pages 2033-2035

Tributylmagnesium ate complex-mediated bromine-magnesium exchange of bromoquinolines: A convenient access to functionalized quinolines

Author keywords

Ate complexes; Exchange reaction; Grignard reagents; Quinoline

Indexed keywords

BROMINE DERIVATIVE; LITHIUM DERIVATIVE; MAGNESIUM DERIVATIVE; ORGANOMETALLIC COMPOUND; QUINOLINE DERIVATIVE; TOLUENE;

EID: 0037416901     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00183-7     Document Type: Article
Times cited : (69)

References (48)
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    • Concerning the bromine-lithium exchange of 2-, 3- and 4-bromoquinolines, see: (a) Gilman, H.; Soddy, T. S. J. Org. Chem. 1957, 22, 565-566; (b) Ishikura, M.; Mano, T.; Oda, I.; Terashima, M. Heterocycles 1984, 22, 2471-2474; (c) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron Lett. 2001, 42, 2907-2910; (d) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron 2002, 58, 3387-3400.
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    • Concerning the bromine-lithium exchange of 2-, 3- and 4-bromoquinolines, see: (a) Gilman, H.; Soddy, T. S. J. Org. Chem. 1957, 22, 565-566; (b) Ishikura, M.; Mano, T.; Oda, I.; Terashima, M. Heterocycles 1984, 22, 2471-2474; (c) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron Lett. 2001, 42, 2907-2910; (d) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron 2002, 58, 3387-3400.
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    • Concerning the bromine-lithium exchange of 2-, 3- and 4-bromoquinolines, see: (a) Gilman, H.; Soddy, T. S. J. Org. Chem. 1957, 22, 565-566; (b) Ishikura, M.; Mano, T.; Oda, I.; Terashima, M. Heterocycles 1984, 22, 2471-2474; (c) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron Lett. 2001, 42, 2907-2910; (d) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron 2002, 58, 3387-3400.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2907-2910
    • Harrowven, D.C.1    Sutton, B.J.2    Coulton, S.3
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    • Concerning the bromine-lithium exchange of 2-, 3- and 4-bromoquinolines, see: (a) Gilman, H.; Soddy, T. S. J. Org. Chem. 1957, 22, 565-566; (b) Ishikura, M.; Mano, T.; Oda, I.; Terashima, M. Heterocycles 1984, 22, 2471-2474; (c) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron Lett. 2001, 42, 2907-2910; (d) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron 2002, 58, 3387-3400.
    • (2002) Tetrahedron , vol.58 , pp. 3387-3400
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    • Wakefield B.J. Organomagnesium Methods in Organic Synthesis. 1995;Academic Press, London, Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E. Eds.; Marcel Dekker: New York, 1996 Grignard Reagents: New Developments; Richey, H. G., Jr., Eds.; Wiley & Sons: New York, 1999.
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    • Concerning the access to pyridylmagnesium reagents through halogen-magnesium exchange, see: (a) Paradies, H. H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem., Int. Ed. Engl. 1969, 8, 279; (b) Paradies, H. H. Naturwissenschaften 1974, 61, 168-169; (c) Martin, G. J.; Mechin, B.; Leroux, Y.; Paulmier, C.; Meunier, J. C. J. Organomet. Chem. 1974, 67, 327-339; (d) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845-5848; (e) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359-1360; (f) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339-4342; (g) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449-7453; (h) Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618-4634; (i) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349-1360; (j) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565-569.
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    • Concerning the access to pyridylmagnesium reagents through halogen-magnesium exchange, see: (a) Paradies, H. H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem., Int. Ed. Engl. 1969, 8, 279; (b) Paradies, H. H. Naturwissenschaften 1974, 61, 168-169; (c) Martin, G. J.; Mechin, B.; Leroux, Y.; Paulmier, C.; Meunier, J. C. J. Organomet. Chem. 1974, 67, 327-339; (d) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845-5848; (e) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359-1360; (f) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339-4342; (g) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449-7453; (h) Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618-4634; (i) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349-1360; (j) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565-569.
    • (1969) Angew. Chem., Int. Ed. Engl. , vol.8 , pp. 279
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    • Concerning the access to pyridylmagnesium reagents through halogen-magnesium exchange, see: (a) Paradies, H. H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem., Int. Ed. Engl. 1969, 8, 279; (b) Paradies, H. H. Naturwissenschaften 1974, 61, 168-169; (c) Martin, G. J.; Mechin, B.; Leroux, Y.; Paulmier, C.; Meunier, J. C. J. Organomet. Chem. 1974, 67, 327-339; (d) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845-5848; (e) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359-1360; (f) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339-4342; (g) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449-7453; (h) Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618-4634; (i) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349-1360; (j) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565-569.
    • (1974) Naturwissenschaften , vol.61 , pp. 168-169
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    • Concerning the access to pyridylmagnesium reagents through halogen-magnesium exchange, see: (a) Paradies, H. H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem., Int. Ed. Engl. 1969, 8, 279; (b) Paradies, H. H. Naturwissenschaften 1974, 61, 168-169; (c) Martin, G. J.; Mechin, B.; Leroux, Y.; Paulmier, C.; Meunier, J. C. J. Organomet. Chem. 1974, 67, 327-339; (d) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845-5848; (e) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359-1360; (f) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339-4342; (g) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449-7453; (h) Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618-4634; (i) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349-1360; (j) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565-569.
    • (1974) J. Organomet. Chem. , vol.67 , pp. 327-339
    • Martin, G.J.1    Mechin, B.2    Leroux, Y.3    Paulmier, C.4    Meunier, J.C.5
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    • Concerning the access to pyridylmagnesium reagents through halogen-magnesium exchange, see: (a) Paradies, H. H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem., Int. Ed. Engl. 1969, 8, 279; (b) Paradies, H. H. Naturwissenschaften 1974, 61, 168-169; (c) Martin, G. J.; Mechin, B.; Leroux, Y.; Paulmier, C.; Meunier, J. C. J. Organomet. Chem. 1974, 67, 327-339; (d) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845-5848; (e) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359-1360; (f) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339-4342; (g) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449-7453; (h) Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618-4634; (i) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349-1360; (j) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565-569.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5845-5848
    • Furukawa, N.1    Shibutani, T.2    Fujihara, H.3
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    • Concerning the access to pyridylmagnesium reagents through halogen-magnesium exchange, see: (a) Paradies, H. H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem., Int. Ed. Engl. 1969, 8, 279; (b) Paradies, H. H. Naturwissenschaften 1974, 61, 168-169; (c) Martin, G. J.; Mechin, B.; Leroux, Y.; Paulmier, C.; Meunier, J. C. J. Organomet. Chem. 1974, 67, 327-339; (d) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845-5848; (e) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359-1360; (f) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339-4342; (g) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449-7453; (h) Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618-4634; (i) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349-1360; (j) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565-569.
    • (1998) Synlett , pp. 1359-1360
    • Bérillon, L.1    Leprêtre, A.2    Turck, A.3    Plé, N.4    Quéguiner, G.5    Cahiez, G.6    Knochel, P.7
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    • Concerning the access to pyridylmagnesium reagents through halogen-magnesium exchange, see: (a) Paradies, H. H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem., Int. Ed. Engl. 1969, 8, 279; (b) Paradies, H. H. Naturwissenschaften 1974, 61, 168-169; (c) Martin, G. J.; Mechin, B.; Leroux, Y.; Paulmier, C.; Meunier, J. C. J. Organomet. Chem. 1974, 67, 327-339; (d) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845-5848; (e) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359-1360; (f) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339-4342; (g) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449-7453; (h) Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618-4634; (i) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349-1360; (j) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565-569.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4339-4342
    • Trécourt, F.1    Breton, G.2    Bonnet, V.3    Mongin, F.4    Marsais, F.5    Quéguiner, G.6
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    • Concerning the access to pyridylmagnesium reagents through halogen-magnesium exchange, see: (a) Paradies, H. H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem., Int. Ed. Engl. 1969, 8, 279; (b) Paradies, H. H. Naturwissenschaften 1974, 61, 168-169; (c) Martin, G. J.; Mechin, B.; Leroux, Y.; Paulmier, C.; Meunier, J. C. J. Organomet. Chem. 1974, 67, 327-339; (d) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845-5848; (e) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359-1360; (f) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339-4342; (g) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449-7453; (h) Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618-4634; (i) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349-1360; (j) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565-569.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 7449-7453
    • Abarbri, M.1    Dehmel, F.2    Knochel, P.3
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    • Concerning the access to pyridylmagnesium reagents through halogen-magnesium exchange, see: (a) Paradies, H. H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem., Int. Ed. Engl. 1969, 8, 279; (b) Paradies, H. H. Naturwissenschaften 1974, 61, 168-169; (c) Martin, G. J.; Mechin, B.; Leroux, Y.; Paulmier, C.; Meunier, J. C. J. Organomet. Chem. 1974, 67, 327-339; (d) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845-5848; (e) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359-1360; (f) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339-4342; (g) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449-7453; (h) Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618-4634; (i) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349-1360; (j) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565-569.
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    • Abarbri, M.1    Thibonnet, J.2    Bérillon, L.3    Dehmel, F.4    Rottländer, M.5    Knochel, P.6
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    • Concerning the access to pyridylmagnesium reagents through halogen-magnesium exchange, see: (a) Paradies, H. H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem., Int. Ed. Engl. 1969, 8, 279; (b) Paradies, H. H. Naturwissenschaften 1974, 61, 168-169; (c) Martin, G. J.; Mechin, B.; Leroux, Y.; Paulmier, C.; Meunier, J. C. J. Organomet. Chem. 1974, 67, 327-339; (d) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845-5848; (e) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359-1360; (f) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339-4342; (g) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449-7453; (h) Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618-4634; (i) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349-1360; (j) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565-569.
    • (2000) Tetrahedron , vol.56 , pp. 1349-1360
    • Trécourt, F.1    Breton, G.2    Bonnet, V.3    Mongin, F.4    Marsais, F.5    Quéguiner, G.6
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    • Concerning the access to pyridylmagnesium reagents through halogen-magnesium exchange, see: (a) Paradies, H. H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem., Int. Ed. Engl. 1969, 8, 279; (b) Paradies, H. H. Naturwissenschaften 1974, 61, 168-169; (c) Martin, G. J.; Mechin, B.; Leroux, Y.; Paulmier, C.; Meunier, J. C. J. Organomet. Chem. 1974, 67, 327-339; (d) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845-5848; (e) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359-1360; (f) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339-4342; (g) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449-7453; (h) Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618-4634; (i) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349-1360; (j) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565-569.
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    • Prepared from isopropylmagnesium chloride and lithium 2,2,6,6-tetramethylpiperidide: Eaton, P. E.; Lee, C.-H.; Xiong, Y. J. Am. Chem. Soc. 1989, 111, 8016-8018.
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    • The physical and spectral data are analogous to those obtained for a commercial sample.
    • The physical and spectral data are analogous to those obtained for a commercial sample.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.