Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ 3-bromane

Masahito Ochiai, Akira Yoshimura, Md Mahbubul Hoque, Takuji Okubo, Motomichi Saito, Kazunori Miyamoto

Результат исследований: Материалы для журналаСтатья

18 Цитирования (Scopus)

Выдержка

Oxidation of primary aliphatic aldehydes with p- trifluoromethylphenyl(difluoro)-λ 3-bromane in dichloromethane at 0 °C afforded acid fluorides selectively in good yields, while that of aromatic aldehydes in chloroform at room temperature produced aryl difluoromethyl ethers. A larger migratory aptitude of aryl groups compared to primary alkyl groups during a 1,2-shift from carbon to an electron-deficient oxygen atom in bromane(III) Criegee-type intermediates will result in these differences in the reaction courses.

Язык оригиналаАнглийский
Страницы (с-по)5568-5571
Число страниц4
ЖурналOrganic Letters
Том13
Номер выпуска20
DOI
СостояниеОпубликовано - 21 окт 2011
Опубликовано для внешнего пользованияДа

Отпечаток

aldehydes
Aldehydes
aptitude
Oxidation
oxidation
Ethers
Methylene Chloride
Chloroform
chloroform
Fluorides
fluorides
ethers
oxygen atoms
Carbon
Electrons
Oxygen
Atoms
acids
Temperature
Acids

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Цитировать

Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ 3-bromane. / Ochiai, Masahito; Yoshimura, Akira; Hoque, Md Mahbubul; Okubo, Takuji; Saito, Motomichi; Miyamoto, Kazunori.

В: Organic Letters, Том 13, № 20, 21.10.2011, стр. 5568-5571.

Результат исследований: Материалы для журналаСтатья

Ochiai, M, Yoshimura, A, Hoque, MM, Okubo, T, Saito, M & Miyamoto, K 2011, 'Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ 3-bromane', Organic Letters, том. 13, № 20, стр. 5568-5571. https://doi.org/10.1021/ol202248x
Ochiai, Masahito ; Yoshimura, Akira ; Hoque, Md Mahbubul ; Okubo, Takuji ; Saito, Motomichi ; Miyamoto, Kazunori. / Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ 3-bromane. В: Organic Letters. 2011 ; Том 13, № 20. стр. 5568-5571.
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abstract = "Oxidation of primary aliphatic aldehydes with p- trifluoromethylphenyl(difluoro)-λ 3-bromane in dichloromethane at 0 °C afforded acid fluorides selectively in good yields, while that of aromatic aldehydes in chloroform at room temperature produced aryl difluoromethyl ethers. A larger migratory aptitude of aryl groups compared to primary alkyl groups during a 1,2-shift from carbon to an electron-deficient oxygen atom in bromane(III) Criegee-type intermediates will result in these differences in the reaction courses.",
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T1 - Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ 3-bromane

AU - Ochiai, Masahito

AU - Yoshimura, Akira

AU - Hoque, Md Mahbubul

AU - Okubo, Takuji

AU - Saito, Motomichi

AU - Miyamoto, Kazunori

PY - 2011/10/21

Y1 - 2011/10/21

N2 - Oxidation of primary aliphatic aldehydes with p- trifluoromethylphenyl(difluoro)-λ 3-bromane in dichloromethane at 0 °C afforded acid fluorides selectively in good yields, while that of aromatic aldehydes in chloroform at room temperature produced aryl difluoromethyl ethers. A larger migratory aptitude of aryl groups compared to primary alkyl groups during a 1,2-shift from carbon to an electron-deficient oxygen atom in bromane(III) Criegee-type intermediates will result in these differences in the reaction courses.

AB - Oxidation of primary aliphatic aldehydes with p- trifluoromethylphenyl(difluoro)-λ 3-bromane in dichloromethane at 0 °C afforded acid fluorides selectively in good yields, while that of aromatic aldehydes in chloroform at room temperature produced aryl difluoromethyl ethers. A larger migratory aptitude of aryl groups compared to primary alkyl groups during a 1,2-shift from carbon to an electron-deficient oxygen atom in bromane(III) Criegee-type intermediates will result in these differences in the reaction courses.

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