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0001571546
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For selected applications of various insoluble polymer supported oxidizing reagents that do not involve the activation of a methyl sulfoxide see: (a) Wade L.G., Stell L.M. J. Chem. Ed. 57:1980;438 (b) Frechet J.M.J., Darling P., Farrall M.J. J. Org. Chem. 46:1981;1728-1730 (c) Bergbreiter D.E., Chandran R. J. Am. Chem. Soc. 107:1985;4792-4793 (d) Hinzen B., Ley S.V. J. Chem. Soc. Perkin Trans. 1. 1997;1907-1908 (e) Dodd D.S., Wallace O.B. Tetrahedron Lett. 39:1998;5701-5704 (f) Ley S.V., Bolli M.H., Hinzen B., Gervois A.G., Hall B.J. J. Chem. Soc. Perkin Trans. 1. 1998;2239-2241 (g) Bhalay G., Dunstan A., Glen A. Synlett. 12:2000;1846-1859.
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0000424260
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For selected applications of various insoluble polymer supported oxidizing reagents that do not involve the activation of a methyl sulfoxide see: (a) Wade L.G., Stell L.M. J. Chem. Ed. 57:1980;438 (b) Frechet J.M.J., Darling P., Farrall M.J. J. Org. Chem. 46:1981;1728-1730 (c) Bergbreiter D.E., Chandran R. J. Am. Chem. Soc. 107:1985;4792-4793 (d) Hinzen B., Ley S.V. J. Chem. Soc. Perkin Trans. 1. 1997;1907-1908 (e) Dodd D.S., Wallace O.B. Tetrahedron Lett. 39:1998;5701-5704 (f) Ley S.V., Bolli M.H., Hinzen B., Gervois A.G., Hall B.J. J. Chem. Soc. Perkin Trans. 1. 1998;2239-2241 (g) Bhalay G., Dunstan A., Glen A. Synlett. 12:2000;1846-1859.
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Frechet, J.M.J.1
Darling, P.2
Farrall, M.J.3
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20
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0000199386
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For selected applications of various insoluble polymer supported oxidizing reagents that do not involve the activation of a methyl sulfoxide see: (a) Wade L.G., Stell L.M. J. Chem. Ed. 57:1980;438 (b) Frechet J.M.J., Darling P., Farrall M.J. J. Org. Chem. 46:1981;1728-1730 (c) Bergbreiter D.E., Chandran R. J. Am. Chem. Soc. 107:1985;4792-4793 (d) Hinzen B., Ley S.V. J. Chem. Soc. Perkin Trans. 1. 1997;1907-1908 (e) Dodd D.S., Wallace O.B. Tetrahedron Lett. 39:1998;5701-5704 (f) Ley S.V., Bolli M.H., Hinzen B., Gervois A.G., Hall B.J. J. Chem. Soc. Perkin Trans. 1. 1998;2239-2241 (g) Bhalay G., Dunstan A., Glen A. Synlett. 12:2000;1846-1859.
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Bergbreiter, D.E.1
Chandran, R.2
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21
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33748733929
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For selected applications of various insoluble polymer supported oxidizing reagents that do not involve the activation of a methyl sulfoxide see: (a) Wade L.G., Stell L.M. J. Chem. Ed. 57:1980;438 (b) Frechet J.M.J., Darling P., Farrall M.J. J. Org. Chem. 46:1981;1728-1730 (c) Bergbreiter D.E., Chandran R. J. Am. Chem. Soc. 107:1985;4792-4793 (d) Hinzen B., Ley S.V. J. Chem. Soc. Perkin Trans. 1. 1997;1907-1908 (e) Dodd D.S., Wallace O.B. Tetrahedron Lett. 39:1998;5701-5704 (f) Ley S.V., Bolli M.H., Hinzen B., Gervois A.G., Hall B.J. J. Chem. Soc. Perkin Trans. 1. 1998;2239-2241 (g) Bhalay G., Dunstan A., Glen A. Synlett. 12:2000;1846-1859.
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Hinzen, B.1
Ley, S.V.2
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22
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0032490896
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For selected applications of various insoluble polymer supported oxidizing reagents that do not involve the activation of a methyl sulfoxide see: (a) Wade L.G., Stell L.M. J. Chem. Ed. 57:1980;438 (b) Frechet J.M.J., Darling P., Farrall M.J. J. Org. Chem. 46:1981;1728-1730 (c) Bergbreiter D.E., Chandran R. J. Am. Chem. Soc. 107:1985;4792-4793 (d) Hinzen B., Ley S.V. J. Chem. Soc. Perkin Trans. 1. 1997;1907-1908 (e) Dodd D.S., Wallace O.B. Tetrahedron Lett. 39:1998;5701-5704 (f) Ley S.V., Bolli M.H., Hinzen B., Gervois A.G., Hall B.J. J. Chem. Soc. Perkin Trans. 1. 1998;2239-2241 (g) Bhalay G., Dunstan A., Glen A. Synlett. 12:2000;1846-1859.
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, vol.39
, pp. 5701-5704
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Dodd, D.S.1
Wallace, O.B.2
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23
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33748718537
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For selected applications of various insoluble polymer supported oxidizing reagents that do not involve the activation of a methyl sulfoxide see: (a) Wade L.G., Stell L.M. J. Chem. Ed. 57:1980;438 (b) Frechet J.M.J., Darling P., Farrall M.J. J. Org. Chem. 46:1981;1728-1730 (c) Bergbreiter D.E., Chandran R. J. Am. Chem. Soc. 107:1985;4792-4793 (d) Hinzen B., Ley S.V. J. Chem. Soc. Perkin Trans. 1. 1997;1907-1908 (e) Dodd D.S., Wallace O.B. Tetrahedron Lett. 39:1998;5701-5704 (f) Ley S.V., Bolli M.H., Hinzen B., Gervois A.G., Hall B.J. J. Chem. Soc. Perkin Trans. 1. 1998;2239-2241 (g) Bhalay G., Dunstan A., Glen A. Synlett. 12:2000;1846-1859.
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Bolli, M.H.2
Hinzen, B.3
Gervois, A.G.4
Hall, B.J.5
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24
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0034533265
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For selected applications of various insoluble polymer supported oxidizing reagents that do not involve the activation of a methyl sulfoxide see: (a)
-
For selected applications of various insoluble polymer supported oxidizing reagents that do not involve the activation of a methyl sulfoxide see: (a) Wade L.G., Stell L.M. J. Chem. Ed. 57:1980;438 (b) Frechet J.M.J., Darling P., Farrall M.J. J. Org. Chem. 46:1981;1728-1730 (c) Bergbreiter D.E., Chandran R. J. Am. Chem. Soc. 107:1985;4792-4793 (d) Hinzen B., Ley S.V. J. Chem. Soc. Perkin Trans. 1. 1997;1907-1908 (e) Dodd D.S., Wallace O.B. Tetrahedron Lett. 39:1998;5701-5704 (f) Ley S.V., Bolli M.H., Hinzen B., Gervois A.G., Hall B.J. J. Chem. Soc. Perkin Trans. 1. 1998;2239-2241 (g) Bhalay G., Dunstan A., Glen A. Synlett. 12:2000;1846-1859.
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Bhalay, G.1
Dunstan, A.2
Glen, A.3
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26
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0001020589
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In related work, an earlier report described the use of an insoluble methyl phenyl sulfoxide reagent that was activated with chlorine
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In related work, an earlier report described the use of an insoluble methyl phenyl sulfoxide reagent that was activated with chlorine Crosby G.A., Weinshenker N.M., Uh H.-S. J. Am. Chem. Soc. 97:1975;2232-2235.
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0001550090
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Harris J.M., Liu Y., Chai S., Andrews M.D., Vederas J.C. J. Org. Chem. 63:1998;2407-2409.
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(a) Enholm E.J., Gallagher M.E., Moran K.M., Lombardi J.S., Schulte J.P. II. Org. Lett. 1:1999;689-691
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(a) Harrison C.R., Hodge P., Hunt B.J., Khoshdel E., Richardson G. J. Org. Chem. 48:1983;3721-3728
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47
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Reed N.N., Delgado M., Hereford K., Clapham B., Janda K.D. Bioorg. Med. Chem. Lett. 12:2002;2047-2049.
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48
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0035803642
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For insoluble polymer bound IBX reagents see: (a) Mülbaier M., Giannis A. Angew. Chem. Int. Ed. 40:2001;4393-4394 (b) Sorg G., Mengei A., Jung G., Rademann J. Angew. Chem. 40:2001;4395-4397.
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Giannis, A.2
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49
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0035803743
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For insoluble polymer bound IBX reagents see: (a)
-
For insoluble polymer bound IBX reagents see: (a) Mülbaier M., Giannis A. Angew. Chem. Int. Ed. 40:2001;4393-4394 (b) Sorg G., Mengei A., Jung G., Rademann J. Angew. Chem. 40:2001;4395-4397.
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Sorg, G.1
Mengei, A.2
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51
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0016439313
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For multipolymer solid-phase peptide synthesis see: (a) Frank H., Hagenmaier H. Experientia. 31:1975;131-133 (b) Heusel G., Bovermann G., Gohring W., Jung G. Angew. Chem. Int. Ed. 16:1977;642-643.
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Hagenmaier, H.2
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52
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0017528090
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For multipolymer solid-phase peptide synthesis see: (a)
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For multipolymer solid-phase peptide synthesis see: (a) Frank H., Hagenmaier H. Experientia. 31:1975;131-133 (b) Heusel G., Bovermann G., Gohring W., Jung G. Angew. Chem. Int. Ed. 16:1977;642-643.
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Heusel, G.1
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53
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0030824025
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For a multipolymer solid-phase sharpless asymmetric dihydroxylation reaction see:
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For a multipolymer solid-phase sharpless asymmetric dihydroxylation reaction see: Han H., Janda K.D. Angew. Chem. Int. Ed. 36:1997;1731-1733.
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Han, H.1
Janda, K.D.2
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56
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85031080700
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Aldrich catalog item, 53,733-0
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Aldrich catalog item, 53,733-0.
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57
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85031067001
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1H NMR analysis using the S-Me group as the signal of reference
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1H NMR analysis using the S-Me group as the signal of reference.
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58
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85031080850
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A reviewer raised the issue that methanol may potentially be oxidized to undesirable formaldehyde during this step. There are several simple means to avoid this issue. One is to use hexanes as the precipitation solvent. When it was used to remove both 3a and 3b from the oxidation of 1-(4-bromophenyl)ethanol, 85 and 70% yields of 4-bromoacetophenone were observed, respectively
-
A reviewer raised the issue that methanol may potentially be oxidized to undesirable formaldehyde during this step. There are several simple means to avoid this issue. One is to use hexanes as the precipitation solvent. When it was used to remove both 3a and 3b from the oxidation of 1-(4-bromophenyl)ethanol, 85 and 70% yields of 4-bromoacetophenone were observed, respectively.
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59
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85031079845
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A reviewer questioned if the use of excess t-BHP would lead to sulfone formation. As a test, thioanisole was allowed to react with 20 equiv. of t-BHP in the presence of AcOH at rt for 2 days. The only product observed was the sulfoxide. Our findings are in agreement with those reported in Ref. 27
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A reviewer questioned if the use of excess t-BHP would lead to sulfone formation. As a test, thioanisole was allowed to react with 20 equiv. of t-BHP in the presence of AcOH at rt for 2 days. The only product observed was the sulfoxide. Our findings are in agreement with those reported in Ref. 27.
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