PREPARATION OF 2-ARYLPROPANOIC ACIDS BY OXIDATIVE ARYL MIGRATION IN (BETA-ARYL-BETA-HYDROXY)ALKYL PHENYL SELENIDES

被引：10

作者：

UEMURA, S ^{[1
]}

OHE, K ^{[1
]}

YAMAUCHI, T ^{[1
]}

MIZUTAKI, S ^{[1
]}

TAMAKI, K ^{[1
]}

机构：

[1] KYOWA HAKKO KOGYO CO LTD,SAKAI RES LAB,SAKAI,OSAKA 590,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 04期

关键词：

D O I：

10.1039/p19900000907

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：907 / 910

页数：4

共 14 条

[1] COMPOUNDS RELATED TO PODOPHYLLOTOXIN .12. PODOPHYLLOTOXONE, PICROPODOPHYLLONE AND DEHYDROPODOPHYLLOTOXIN [J].

GENSLER, WJ ;

JOHNSON, F ;

SLOAN, ADB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (23) :6074-6081

[2] SYNTHESIS OF ANTI-INFLAMMATORY ALPHA-ARYLALKANOIC ACIDS BY 1,2-ARYL SHIFT [J].

GIORDANO, C ;

CASTALDI, G ;

UGGERI, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (06) :413-419

[3]

LEONARDCOPPENS AM, 1976, TETRAHEDRON LETT, P3227

[4] SYNTHESIS OF UNSYMMETRICAL TELLURIDES AND SELENADITELLURIDES [J].

PETRAGNANI, N ;

TORRES, L ;

WYNNE, KJ .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 92 (02) :185-189

[5]

REMION J, 1976, TETRAHEDRON LETT, P3743

[6] METHODS FOR THE SYNTHESIS OF ANTIINFLAMMATORY 2-ARYL PROPIONIC ACIDS [J].

RIEU, JP ;

BOUCHERLE, A ;

COUSSE, H ;

MOUZIN, G .

TETRAHEDRON, 1986, 42 (15) :4095-4131

[7] ALPHA-(PHENYLSELENO)METHYLLITHIUM COMPOUNDS [J].

SEEBACH, D ;

PELETIES, N .

CHEMISCHE BERICHTE-RECUEIL, 1972, 105 (02) :511-&

[8] MONO-, BIS-, AND TRIS(PHENYLSELENO)METHYLLITHIUM (SELENIUM-STABILIZED CARBANIONS) [J].

SEEBACH, D ;

PELETIES, N .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (06) :450-&

[9] ELECTROPHILIC AND NUCLEOPHILIC ORGANOSELENIUM REAGENTS - NEW ROUTES TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].

SHARPLES.KB ;

LAUER, RF ;

TERANISH.AY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (18) :6137-6139

[10] PHENYLSELENENYL CHLORIDE IN ACETONITRILE WATER - A HIGHLY CONVENIENT REAGENT FOR HYDROXYSELENATION OF OLEFINS AND PREPARATION OF CYCLIC ETHERS FROM DIENES [J].

TOSHIMITSU, A ;

AOAI, T ;

OWADA, H ;

UEMURA, S ;

OKANO, M .

TETRAHEDRON, 1985, 41 (22) :5301-5306

← 1 2 →