Fluoridation of heteroaromatic iodonium salts -: experimental evidence supporting theoretical prediction of the selectivity of the process

被引：81

作者：

Martín-Santamaría, S

Carroll, MA

Carroll, CM

Carter, CD

Pike, VW

Rzepa, HS ^{[1
]}

Widdowson, DA

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England

[2] Hammersmith Hosp, Imperial Coll Sch Med, MRC Cyclotron Unit, Chem & Engn Grp, London W12 0NN, England

来源：

CHEMICAL COMMUNICATIONS | 2000年 / 08期

关键词：

D O I：

10.1039/b000868k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Theoretical prediction, that the nucleophilic substitution of a range of arylheteroaryliodonium salts by fluoride ion is regioselective for the aryl ring with the exception of benzo[b]furan, are borne out by experimental observation.

引用

页码：649 / 650

页数：2

共 17 条

[1] An ab initio and MNDO-d SCF-MO computational study of stereoelectronic control in extrusion reactions of R2I-F iodine(III) intermediates [J].

Carroll, MA ;

Martín-Santamaría, S ;

Pike, VW ;

Rzepa, HS ;

Widdowson, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (12) :2707-2714

[2]

CARROLL MA, UNPUB

[3]

Ermolenko M. S., 1978, J HETEROCYCLIC CHEM, P752

[4] DOPAMINE VISUALIZED IN THE BASAL GANGLIA OF LIVING MAN [J].

GARNETT, ES ;

FIRNAU, G ;

NAHMIAS, C .

NATURE, 1983, 305 (5930) :137-138

[5] UNIFIED MECHANISTIC ANALYSIS OF POLAR REACTIONS OF DIARYLIODONIUM SALTS [J].

GRUSHIN, VV ;

DEMKINA, II ;

TOLSTAYA, TP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (04) :505-511

[6] CARBORANYLHALONIUM IONS - FROM STRIKING REACTIVITY TO A UNIFIED MECHANISTIC ANALYSIS OF POLAR REACTIONS OF DIARYLHALONIUM COMPOUNDS [J].

GRUSHIN, VV .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (11) :529-536

[7]

GUILLAUME M, 1991, APPL RADIAT ISOTOPES, V42, P749, DOI 10.1016/0883-2889(91)90179-5

[8]

LUXEN A, 1992, NUCL MED BIOL, V19, P149, DOI 10.1016/0883-2897(92)90002-G

[9]

PHELPS ME, 1986, POSITRON EMISSION TO

[10] REACTIONS OF CYCLOTRON-PRODUCED [F-18] FLUORIDE WITH DIARYLIODONIUM-SALTS - A NOVEL SINGLE-STEP ROUTE TO NO-CARRIER-ADDED [(18)]FLUOROARENES [J].

PIKE, VW ;

AIGBIRHIO, FI .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (21) :2215-2216

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