CATALYTIC AMINOMERCURATION OF OLEFINS IN A TANDEM AMINOMERCURATION-DEOXYMERCURATION - ONE-STEP SYNTHESIS OF SECONDARY N-ARYLALLYLAMINES FROM ALLYLALCOHOLS

被引：8

作者：

BARLUENGA, J

PEREZPRIETO, J

ASENSIO, G

机构：

[1] UNIV VALENCIA,FAC FARM,DEPT QUIM ORGAN,AVDA BLASCO IBANEZ 13,E-46010 VALENCIA,SPAIN

[2] UNIV OVIEDO,FAC QUIM,DEPT QUIM ORGANOMETAL,E-33006 OVIEDO,SPAIN

来源：

TETRAHEDRON | 1990年 / 46卷 / 07期

关键词：

D O I：

10.1016/S0040-4020(01)82026-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allyl alcohols react with primary aromatic amines and stoichiometric amounts of mercury(II) tetrafluoroborate to give mixtures of mono- and diallyl anilines. However, the use of the tandem aminomercuration-deoxymercuration promoted by catalytic mercury(II) tetrafluoroborate allows to perform regiospecifically the monoallylation reaction with very high yields. A mechanism is proposed to account for the observed results. © 1990.

引用

页码：2453 / 2460

页数：8

共 20 条

[1] ARZOUMANIAN H, 1971, SYNTH-INT J METHODS, P527
[2] MERCURY(II) OXIDE TETRAFLUOROBORIC ACID - AN UNUSUAL BEHAVIOR IN THE OXIDATION OF ALKENES - SYNTHESIS OF TRANS-CINNAMYLETHERS
BARLUENGA, J
ALONSOCIRES, L
ASENSIO, G
[J]. TETRAHEDRON LETTERS, 1981, 22 (23) : 2239 - 2240
[3] ALKOXYMERCURIATION OF CONJUGATED DIENES - REGIO-SELECTIVE AND STEREO-SELECTIVE SYNTHESIS OF UNSATURATED DIETHERS
BARLUENGA, J
PEREZPRIETO, J
ASENSIO, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (04): : 629 - 633
[4] MERCURY(II) OXIDE TETRAFLUOROBORIC ACID-PROMOTED 1,4-CYCLOAMINATION OF 1,3-DIENES - SYNTHESIS OF 9-AZABICYCLO[4.2.1]NON-7-ENES AND 3-PYRROLINES
BARLUENGA, J
PEREZPRIETO, J
ASENSIO, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (20) : 1181 - 1182
[5] THE QUESTION OF THE REVERSIBILITY IN THE AMINOMERCURATION OF OLEFINS - SYNTHESIS OF N-ARYL-9-AZABICYCLO[4.2.1] AND [3.3.1] NONANES BY AMINOMERCURATION OF CIS-CIS-1,5-CYCLOOCTADIENE
BARLUENGA, J
PEREZPRIETO, J
BAYON, AM
ASENSIO, G
[J]. TETRAHEDRON, 1984, 40 (07) : 1199 - 1204
[6] BARLUENGA J, 1979, SYNTHESIS-STUTTGART, P962
[7] BARLUENGA J, 1981, SYNTHESIS-STUTTGART, P376
[8] BETA-SUBSTITUTED ORGANOALKALINE TRI-ANIONS AND TETRA-ANIONS - PREPARATION, STABILITY, AND REACTIVITY
BARLUENGA, J
FANANAS, FJ
VILLAMANA, J
YUS, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (12): : 2685 - 2692
[9] UNEXPECTED REACTIVITY OF ALLYL MAGNESIUM-CHLORIDE WITH NITROARENES - A GENERAL-METHOD OF SYNTHESIS OF N-ALLYL-N-ARYLHYDROXYLAMINES AND N-ALLYLANILINES
BARTOLI, G
MARCANTONI, E
BOSCO, M
DALPOZZO, R
[J]. TETRAHEDRON LETTERS, 1988, 29 (18) : 2251 - 2254
[10] SOLVOMERCURATION-DEMERCURATION .1. OXYMERCURATION-DEMERCURATION OF REPRESENTATIVE OLEFINS IN AN AQUEOUS SYSTEM - A CONVENIENT MILD PROCEDURE FOR MARKOVNIKOV HYDRATION OF CARBON-CARBON DOUBLE BOND
BROWN, HC
GEOGHEGA.PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) : 1844 - &

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