Preparation of 2-arylpropanoic acids by oxidative aryl migration in (β-aryl-β-hydroxy)alkyl phenyl selenides

Preparation of 2-arylpropanoic acids by oxidative aryl migration in (β-aryl-β-hydroxy)alkyl phenyl selenides
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DOI:
10.1039/p19900000907
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发表时间:
1990
期刊:
Journal of The Chemical Society-perkin Transactions 1
影响因子:
--
通讯作者:
S. Uemura;K. Ohe;T. Yamauchi;S. Mizutaki;K. Tamaki
S. Uemura;K. Ohe;T. Yamauchi;S. Mizutaki;K. Tamaki
中科院分区:
其他
文献类型:
--
作者:
S. Uemura;K. Ohe;T. Yamauchi;S. Mizutaki;K. Tamaki

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Oxidation of diastereoisomeric mixtures of 1-aryl-1-hydroxyprop-2-yl phenyl selenides, prepared either by phenylselenenylation of propiophenones followed by reduction or by treatment of benzaldehyde with α-(phenylseleno)ethyl anion, with an excess of meta-chloroperbenzoic acid in methanol at 25 °C for 24 h or at reflux for 2 h affords methyl 2-arylpropanoates almost quantitatively. Similar treatment in tetrahydrofuran at 25 °C for 24 h results in a direct formation of 2-arylpropanoic acids in high yields.