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Volumn 59, Issue 36, 2003, Pages 7171-7176

Soluble polystyrene-based sulfoxide reagents for Swern oxidation reactions

Author keywords

Polymer; Swern oxidation; tert butyl hydroperoxide

Indexed keywords

POLYSTYRENE; SULFOXIDE; TERT BUTYL HYDROPEROXIDE;

EID: 0042020349     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01105-0     Document Type: Article
Times cited : (34)

References (60)
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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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    • 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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    • Aldrich catalog item, 53,733-0
    • Aldrich catalog item, 53,733-0.
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    • 1H NMR analysis using the S-Me group as the signal of reference
    • 1H NMR analysis using the S-Me group as the signal of reference.
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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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    • 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
    • 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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