Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX)

Organic Letters

Volumn 4, Issue 2, 2002, Pages 285-288

  Magdziak, Derek ^a   Rodriguez, Andy A ^a   Van De Water, Ryan W ^a   Pettus, Thomas R R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 IODYLBENZOIC ACID; 2-IODOXYBENZOIC ACID; CATECHOL DERIVATIVE; IODOBENZOIC ACID DERIVATIVE; PHENOL DERIVATIVE; QUINONE DERIVATIVE;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

CATECHOLS; IODOBENZOATES; OXIDATION-REDUCTION; PHENOLS; QUINONES;

EID: 0037165401     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017068j     Document Type: Article

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21. (V)] intermediate in the synthesis of Dess-Martin periodinane, has gained popularity in its own right as mild oxidant for alcohols, particularly diols, and for the selective oxidations of the carbon atom adjacent to aromatic systems, when 1 is applied in polar solvents: (a) Chaudhari, S. S. Synlett 2000, (2), 278.
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25. Phenol itself failed to undergo oxidation with IBX.
26. No correction was made for differences between the relaxation times of the examined proton in the product and standard. However, protons with similar characteristics and in similar chemical environments were compared if possible. The crude spectra that are available for 6, 8, 11, 13, 15, 17, and 19 contain the 2-iodobenzoic acid byproduct of IBX.
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