GENERATION OF ARYL RADICALS BY THE OXIDATION OF ALPHA-(ARYLAZO)TRIPHENYLMETHANES BY CERIUM(IV) AMMONIUM-NITRATE

被引：7

作者：

ARAI, N ^{[1
]}

NARASAKA, K ^{[1
]}

机构：

[1] UNIV TOKYO, GRAD SCH SCI, DEPT CHEM, BUNKYO KU, TOKYO 113, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1995年 / 68卷 / 06期

关键词：

D O I：

10.1246/bcsj.68.1707

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The one-electron oxidation of alpha-(arylazo)triphenylmethanes by cerium(IV) ammonium nitrate (CAN) generated aryl radicals along with the triphenylmethyl cation. When the reaction was carried out in the presence of appropriate radical-trapping agents, such as arenes and olefins, the corresponding addition products were obtained in moderate yield. The oxidation of the arylazo compounds with CAN was accelerated by the addition of acids.

引用

页码：1707 / 1714

页数：8

共 39 条

[1] AROMATIC SUBSTITUTION .22. POLARITY OF ARYL RADICALS [J].

ABRAMOVI.RA ;

KOLEOSO, OA .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1969, (06) :779-+

[2] ARYLATIONS USING DIAZONIUM TETRAFLUOROBORATE AND PYRIDINE - A CONVENIENT SOURCE OF ARYL RADICALS [J].

ABRAMOVI.RA ;

SAHA, JG .

TETRAHEDRON, 1965, 21 (12) :3297-&

[3] DUALITY OF MECHANISM IN THE OXIDATION OF ALKENYLBENZENES BY CERIUM(IV) AMMONIUM-NITRATE [J].

BACIOCCHI, E ;

ROL, C ;

SEBASTIANI, GV ;

ZAMPINI, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (18) :1045-1047

[4] PHASE-TRANSFER-CATALYZED GOMBERG-BACHMANN SYNTHESIS OF UNSYMMETRICAL BIARENES - A SURVEY OF CATALYSTS AND SUBSTRATES [J].

BEADLE, JR ;

KORZENIOWSKI, SH ;

ROSENBERG, DE ;

GARCIASLANGA, BJ ;

GOKEL, GW .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) :1594-1603

[5] IODODEDIAZONIATION OF ARENEDIAZONIUM SALTS ACCOMPANIED BY ARYL RADICAL RING-CLOSURE [J].

BECKWITH, ALJ ;

MEIJS, GF .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10) :1922-1930

[6]

BECKWITH ALJ, 1975, J CHEM SOC P2, P693

[7] ELECTRICAL EFFECTS IN THE BIPHENYL AND NAPHTHALENE SYSTEMS - THE INFLUENCE OF ALKYL GROUPS ATTACHED TO SILICON ON DESILYLATION REACTIONS [J].

BENKESER, RA ;

SCHROEDER, W ;

THOMAS, OH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (09) :2283-2287

[8] DIRECTIVE EFFECTS IN ATTACK OF PHENYL RADICALS ON CARBON-HYDROGEN BONDS [J].

BRIDGER, RF ;

RUSSELL, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (23) :3754-&

[9]

CHAWLA HM, 1985, SYNTHESIS-STUTTGART, P70

[10] THE EFFECTS OF STRUCTURE ON THE KINETICS OF DECOMPOSITION OF SUBSTITUTED PHENYL-AZOTRIPHENYLMETHANES [J].

COHEN, SG ;

WANG, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (22) :5504-5507

← 1 2 3 4 →