20734-74-1Relevant articles and documents
Photochemical Lumiketone-Type Rearrangement of 3-Methoxyphenol Promoted by AlBr3
Kakiuchi, Kiyomi,Ue, Masaki,Yamaguchi, Bunji,Nishimoto, Atsushi,Tobe, Yoshito
, p. 3468 - 3470 (1991)
Irradition of 3-methoxyphenol in the presence of 2 equiv. of AlBr3 in CH2Cl2 gave 4-methoxybicyclohex-3-en-2-one in a 38percent yield. 3-Methoxy-2-methylphenol also yielded the lumiketone rearrangement product.On the other hand, 3-methoxy-4-methyl-, 3-methoxy-5-methyl-, and 5-methoxy-2-methylphenol underwent transposition of the methyl group to give equilibrium mixtures of the three methoxycresoles.
A convenient synthesis of phenols
Kristianslund, Renate,Vik, Anders,Hansen, Trond V.
supporting information, p. 2809 - 2814 (2018/12/04)
Anilines are rapidly, often within 60 minutes, converted into the corresponding phenols in up to 87% isolated yield. The presented experimentally simple protocol display broad compatibility with a variety of functional groups, and in particular, well suited for the preparation of methyl-substituted phenols. Such phenols are not easily available by other synthetic approaches. The formation of phenolic radical coupling products was not observed even for activated anilines using this open flask method.
Metal-free oxidation of aromatic carbon-hydrogen bonds through a reverse-rebound mechanism
Yuan, Changxia,Liang, Yong,Hernandez, Taylor,Berriochoa, Adrian,Houk, Kendall N.,Siegel, Dionicio
, p. 192 - 196 (2013/08/23)
Methods for carbon-hydrogen (C-H) bond oxidation have a fundamental role in synthetic organic chemistry, providing functionality that is required in the final target molecule or facilitating subsequent chemical transformations. Several approaches to oxidizing aliphatic C-H bonds have been described, drastically simplifying the synthesis of complex molecules. However, the selective oxidation of aromatic C-H bonds under mild conditions, especially in the context of substituted arenes with diverse functional groups, remains a challenge. The direct hydroxylation of arenes was initially achieved through the use of strong Bronsted or Lewis acids to mediate electrophilic aromatic substitution reactions with super-stoichiometric equivalents of oxidants, significantly limiting the scope of the reaction. Because the products of these reactions are more reactive than the starting materials, over-oxidation is frequently a competitive process. Transition-metal-catalysed C-H oxidation of arenes with or without directing groups has been developed, improving on the acid-mediated process; however, precious metals are required. Here we demonstrate that phthaloyl peroxide functions as a selective oxidant for the transformation of arenes to phenols under mild conditions. Although the reaction proceeds through a radical mechanism, aromatic C-H bonds are selectively oxidized in preference to activated-H bonds. Notably, a wide array of functional groups are compatible with this reaction, and this method is therefore well suited for late-stage transformations of advanced synthetic intermediates. Quantum mechanical calculations indicate that this transformation proceeds through a novel addition-abstraction mechanism, a kind of 'reverse-rebound' mechanism as distinct from the common oxygen-rebound mechanism observed for metal-oxo oxidants. These calculations also identify the origins of the experimentally observed aryl selectivity.
IMIDAZOLIDINEDIONE DERIVATIVES
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, (2011/06/26)
The invention provides a compound of formula (Ia), and pharmaceutically acceptable salts thereof. The invention also provides use of the compounds or salts as modulators of Kv3.1 and/or Kv3.2, and in the treatment of diseases or disorders where a modulator of Kv3.1 and/or Kv3.2 is required, such as depression and mood disorders, hearing disorders, schizopherenea, substance abuse disorders, sleep disorders or epilepsy.
