NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - DIRECT 1,2-BIS-AZIDONATION OF TRIISOPROPYLSILYL ENOL ETHERS - AN AZIDO-RADICAL ADDITION PROCESS PROMOTED BY TEMPO

被引：45

作者：

MAGNUS, P

ROE, MB

HULME, C

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 02期

关键词：

D O I：

10.1039/c39950000263

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of triisopropylsilyl enol ethers with PhIO/MSN(3)/TEMPO (cat.) -45 degrees C results in 1,2-bis-azidonation, which appears to occur through a radical addition process; the 1-azido group can be replaced by carbon nucleophiles such as allyl, methyl, cyano, acetylene and acetonyl.

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页码：263 / 265

页数：3

相关论文

共 32 条

[1]

ARIMOTO M, 1989, CHEM PHARM BULL, V37, P3221

[2] 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

[3] THE FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .20. ALKYL HYDROPEROXIDES - REACTION INTERMEDIATES IN THE OXIDATION OF SATURATED-HYDROCARBONS BY GIF-TYPE REACTIONS AND MECHANISTIC STUDIES ON THEIR FORMATION [J].

BARTON, DHR ;

BEVIERE, SD ;

CHAVASIRI, W ;

CSUHAI, E ;

DOLLER, D ;

LIU, WG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) :2147-2156

[4] MECHANISM OF THE GIF-BARTON TYPE ALKANE FUNCTIONALIZATION BY HALIDE AND PSEUDOHALIDE IONS - COMMENTS [J].

BARTON, DHR ;

HILL, DR .

TETRAHEDRON LETTERS, 1994, 35 (09) :1431-1434

[5] KINETICS OF THE COUPLING REACTIONS OF THE NITROXYL RADICAL 1,1,3,3-TETRAMETHYLISOINDOLINE-2-OXYL WITH CARBON-CENTERED RADICALS [J].

BECKWITH, ALJ ;

BOWRY, VW ;

MOAD, G .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1632-1641

[6]

BIRKOFER L, 1975, LIEBIGS ANN CHEM, P266

[7]

BLANDY C, 1983, TETRAHEDRON LETT, P4189

[8] CALIBRATION OF A NEW HOROLOGERY OF FAST RADICAL CLOCKS - RING-OPENING RATES FOR RING-ALKYL-SUBSTITUTED AND ALPHA-ALKYL-SUBSTITUTED CYCLOPROPYLCARBINYL RADICALS AND FOR THE BICYCLO[2.1.0]PENT-2-YL RADICAL [J].

BOWRY, VW ;

LUSZTYK, J ;

INGOLD, KU .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (15) :5687-5698

[9] CALIBRATION OF THE BICYCLO[2.1.0]PENT-2-YL RADICAL RING-OPENING AND AN OXYGEN REBOUND RATE-CONSTANT FOR CYTOCHROME-P-450 [J].

BOWRY, VW ;

LUSZTYK, J ;

INGOLD, KU .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) :1927-1928

[10] ABSOLUTE RATE CONSTANTS FOR THE REACTIONS OF SOME CARBON-CENTERED RADICALS WITH 2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL [J].

CHATEAUNEUF, J ;

LUSZTYK, J ;

INGOLD, KU .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1629-1632

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