HYPERVALENT IODINE-INDUCED NUCLEOPHILIC-SUBSTITUTION OF PARASUBSTITUTED PHENOL ETHERS - GENERATION OF CATION RADICALS AS REACTIVE INTERMEDIATES

被引：412

作者：

KITA, Y ^{[1
]}

TOHMA, H ^{[1
]}

HATANAKA, K ^{[1
]}

TAKADA, T ^{[1
]}

FUJITA, S ^{[1
]}

MITOH, S ^{[1
]}

SAKURAI, H ^{[1
]}

OKA, S ^{[1
]}

机构：

[1] KYOTO PHARMACEUT UNIV,YAMASHINA KU,KYOTO 607,JAPAN

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1994年 / 116卷 / 09期

关键词：

D O I：

10.1021/ja00088a003

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel hypervalent iodine induced nucleophilic substitution of para-substituted phenol ethers in the presence of a variety of nucleophiles is described. UV and ESR spectroscopic studies indicate that this reaction proceeds via cation radicals, [ArH.+], as reactive intermediates generated by single-electron transfer (SET) from a charge-transfer (dT) complex of phenol ethers with phenyliodine(III) bis(trifluoroacetate) (PIFA). This is the first case that involves a radical intermediate on hypervalent iodine oxidations of aromatic compounds.

引用

收藏

页码：3684 / 3691

页数：8

相关论文

共 72 条

[1] IODOSYLBENZENE-TRIMETHYLSILYL AZIDE-BORON TRIFLUORIDE ETHERATE - A HIGHLY EFFICIENT SYSTEM FOR DIRECT SYNTHESIS OF ALLYL AZIDES FROM ALLYLSILANES [J].

ARIMOTO, M ;

YAMAGUCHI, H ;

FUJITA, E ;

OCHIAI, M ;

NAGAO, Y .

TETRAHEDRON LETTERS, 1987, 28 (50) :6289-6292

[2] ORGANIC POLYVALENT IODINE COMPOUNDS [J].

BANKS, DF .

CHEMICAL REVIEWS, 1966, 66 (03) :243-&

[3] SPIRANS .12. STEREOCHEMICAL CONTROL IN THE OXIDATIVE CYCLIZATION OF BIS-NAPHTHOLS [J].

BENNETT, DJ ;

DEAN, FM ;

HERBIN, GA ;

MATKIN, DA ;

PRICE, AW ;

ROBINSON, ML .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (09) :1978-1985

[4] DIARYLIODONIUM SALTS .2. THE PHENYLATION OF ORGANIC AND INORGANIC BASES [J].

BERINGER, FM ;

BRIERLEY, A ;

DREXLER, M ;

GINDLER, EM ;

LUMPKIN, CC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (11) :2708-2712

[5]

BHATT MV, 1986, INDIAN J CHEM B, P1004

[6] SPIRO-ANNULATED 2,5-CYCLOHEXADIENONES VIA OXIDATION OF 2'-ALKENYL-PARA-PHENYL PHENOLS WITH IODOBENZENE DIACETATE [J].

CALLINAN, A ;

CHEN, Y ;

MORROW, GW ;

SWENTON, JS .

TETRAHEDRON LETTERS, 1990, 31 (32) :4551-4552

[7] SPIRANS .13. THE SYNTHESIS AND ORIENTATION OF SPIRANS RELATED TO ABELS KETONE (NAPHTHO[2,1-B]FURAN-2(1H)-SPIRO-1'(2'H)-NAPHTHALEN-2'-ONE) [J].

DEAN, FM ;

HERBIN, GA ;

MATKIN, DA ;

PRICE, AW ;

ROBINSON, ML .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (09) :1986-1993

[8] A NOVEL AND MILD SOURCE OF CARBON-CENTERED RADICALS BY IODOSOBENZENE DIACETATE (IBDA) AND SODIUM-AZIDE FROM ALCOHOLS, ETHERS, ALDEHYDES, AMIDES AND ALKYL IODIDES [J].

FONTANA, F ;

MINISCI, F ;

YAN, YM ;

ZHAO, LH .

TETRAHEDRON LETTERS, 1993, 34 (15) :2517-2520

[9] AN ELECTRON SPIN RESONANCE STUDY OF RADICAL CATIONS OF SOME P-DIALKOXYBENZENES [J].

FORBES, WF ;

SULLIVAN, PD ;

WANG, HM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (11) :2705-&

[10] OXIDATIONS WITH PHENYL IODOSOACETATE .6. THE OXIDATION OF SOME PHENOLS CONTAINING ELECTRON-ATTRACTING SUBSTITUENTS [J].

FOX, AR ;

PAUSACKER, KH .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (JAN) :295-301

← 1 2 3 4 5 6 7 8 →