AZIDE-CATALYZED REARRANGEMENT OF N-(ARYLOXY)PYRIDINIUM SALTS - FACILE SYNTHESIS OF 3-(O-HYDROXYPHENYL)PYRIDINES

被引：6

作者：

ABRAMOVITCH, RA ^{[1
]}

MILLER, AL ^{[1
]}

RADZIKOWSKA, TA ^{[1
]}

TOMASIK, P ^{[1
]}

机构：

[1] PEDAGOGICAL UNIV, PL-42201 CZESTOCHOWA, POLAND

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 03期

关键词：

D O I：

10.1021/jo01317a040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-(Aryloxy)pyridinium tetrafluoroborates react with azide (and other) ions in solution to give good yields of 3-(o-hydroxyphenyl)pyridines under mild conditions; the rearrangements may be rationalized by invoking either a 3, 5 shift or a homolysis and radical recombination. © 1979, American Chemical Society. All rights reserved.

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页码：464 / 465

页数：2

相关论文

共 14 条

[1] THERMOLYSIS OF ARYLOXYPYRIDINIUM SALTS - POSSIBLE GENERATION OF ARYLOXENIUM IONS [J].

ABRAMOVI.RA ;

INBASEKA.M ;

KATO, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (16) :5428-5430

[2] N-ARYLOXYPYRIDINIUM SALTS AND THEIR BASE-CATALYZED REARRANGEMENT [J].

ABRAMOVITCH, RA ;

KATO, S ;

SINGER, GM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :3074-+

[3] BENZISOXAZOLO[2,3-ALPHA]PYRIDINIUM TETRAFLUOROBORATES - POSSIBLE GENERATION OF AN ARYLOXENIUM ION [J].

ABRAMOVITCH, RA ;

INBASEKARAN, MN .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (03) :149-150

[4] REACTION OF PYRIDINE 1-OXIDES AND N-IMINOPYRIDINIUM YLIDES WITH DIAZONIUM SALTS N-ARYLOXYPYRIDINIUM SALTS AND THEIR BASE-CATALYZED REARRANGEMENT [J].

ABRAMOVITCH, RA ;

INBASEKARAN, MN ;

KATO, S ;

SINGER, GM .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (10) :1717-1724

[5]

ABRAMOVITCH RA, 1977, TETRAHEDRON LETT, P1109

[6]

ABRAMOVITCH RA, 1974, PYRIDINE ITS DERIV 1, P58

[7]

Butterworth EC, 1940, J CHEM SOC, P349

[8] CYANATION OF AMINE OXIDE SALTS - A NEW SYNTHESIS OF CYANOPYRIDINES [J].

FEELY, WE ;

BEAVERS, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (15) :4004-4007

[9] PYRIDINES .38. REACTION OF 1-ALKOXYPYRIDINIUM AND 1-ALKOXY-3-ALKYLPYRIDINIUM HALIDES WITH POTASSIUM CYANIDE [J].

FERLES, M ;

JANKOVSK.M .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1968, 33 (11) :3848-&

[10] N-OXIDES AND RELATED COMPOUNDS .35. REACTIONS OF N-ALKOXY-PYRIDINIUM AND -QUINOLINIUM CATIONS WITH NUCLEOPHILES [J].

KATRITZKY, AR ;

LUNT, E .

TETRAHEDRON, 1969, 25 (18) :4291-+