NUCLEOPHILIC COUPLING OF ALKALI 2-NAPHTHOXIDES WITH 1-BROMO-2-NAPHTHOLS - ION-PAIRING AND HALOGEN DANCE IN THE FORMATION OF 1,1'-BINAPHTHALENE-2,2'-DIOLS

被引：11

作者：

BELOHRADSKY, M ^{[1
]}

HOLY, P ^{[1
]}

ZAVADA, J ^{[1
]}

机构：

[1] ACAD SCI CZECH REPUBL,INST ORGAN CHEM & BIOCHEM,CR-16610 PRAGUE 6,CZECH REPUBLIC

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1995年 / 10期

关键词：

D O I：

10.1039/p29950001853

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A very pronounced effect of solvent and cation has been found in the investigated reaction, indicating that ion-pairing is indispensable in the title product formation. A simple rationale has been provided assuming self-assembly of the complementary reactants driven by hydrogen bonding and ion-pairing interactions. Concomitantly, halogen exchange between the reaction partners has been demonstrated to be a concurrent pathway, resulting from the nucleophilic 2-naphthoxide attack at the bromine terminus of the C-alpha-Br bond in the participating 1-bromo-2-naphthol.

引用

页码：1853 / 1856

页数：4

共 21 条

[1]

Albert A., 1971, IONIZATION CONSTANTS

[2] THE REACTIVITY OF OXYGEN NUCLEOPHILES WITH ARYL RADICALS IN THE S(RN)1 MECHANISM [J].

BAUMGARTNER, MT ;

PIERINI, AB ;

ROSSI, RA .

TETRAHEDRON LETTERS, 1992, 33 (17) :2323-2326

[3] SRN1 STUDIES .23. COUPLING OF IODONAPHTHALENES WITH NAPHTHOXIDE IONS UNDER SRN1 CONDITIONS - SYNTHESIS OF UNSYMMETRICAL BINAPHTHYL DERIVATIVES [J].

BEUGELMANS, R ;

BOISCHOUSSY, M ;

TANG, Q .

TETRAHEDRON LETTERS, 1988, 29 (14) :1705-1708

[4] SRN1 REACTIONS .22. PHENOXIDE AND NAPHTHOXIDE IONS AS NUCLEOPHILES FOR SRN1 REACTIONS - SYNTHESIS OF BIPHENYL AND PHENYLNAPHTHYL DERIVATIVES [J].

BEUGELMANS, R ;

BOISCHOUSSY, M .

TETRAHEDRON LETTERS, 1988, 29 (11) :1289-1292

[5] THE ROLE OF SINGLE-ELECTRON TRANSFER IN SN2-TYPE SUBSTITUTION-REACTIONS OF ANIONS WITH ALKYL-HALIDES [J].

BORDWELL, FG ;

HARRELSON, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (20) :4893-4898

[6] REACTIVITY OF HALOGENONAPHTHOLS TOWARDS NUCLEOPHILES .2. KINETICS AND MECHANISMS OF REACTIONS OF 1-HALOGENO-2-NAPHTHOLS WITH ANILINES [J].

BOSCO, M ;

TODESCO, PE .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (09) :1742-&

[7]

BOSCO M, 1967, GAZZ CHIM ITAL, V97, P1594

[8] THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].

BRINGMANN, G ;

WALTER, R ;

WEIRICH, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991

[9]

BUNNETT JF, 1972, ACCOUNTS CHEM RES, V5, P129

[10] SELF-CONDENSATION OF 1-BROMO-2-NAPHTHOL - MECHANISM OF FORMATION OF A 1,4-DINAPHTHODIOXIN [J].

FORLANI, L ;

LUGLI, A ;

NANNI, D ;

TODESCO, PE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (06) :1291-1293

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