SIDE-CHAIN METALATION OF DIETHYL PHOSPHONOTOLUENES

被引：3

作者：

BOUMEKOUEZ, A ^{[1
]}

ABOUTJAUDET, E ^{[1
]}

COLLIGNON, N ^{[1
]}

机构：

[1] IRCOF,INSA,COMPOSES ORGANOPHOSPHORES LAB,F-76131 MONT ST AIGNAN,FRANCE

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1994年 / 466卷 / 1-2期

关键词：

PHOSPHORUS; METALATION; TOLUENE;

D O I：

10.1016/0022-328X(94)88032-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Ortho and para-diethylphosphonotoluenes are regioselectively lithiated using lithium diisopropylamide in tetrahydrofuran at -70 degrees C at the benzylic positions. The lithiated species react with para-anisaldehyde or chlorotrimethylsilane to give the corresponding carbinols or trimethylsilylated derivatives in excellent yields. In contrast, the extent of metallation of meta-diethylphosphonotoluene does not exceed 60% under the same conditions.

引用

页码：89 / 94

页数：6

共 19 条

[1] SYNTHESIS OF 4-PHOSPHONO-DL-PHENYLALANINE AND OF 4-(PHOSPHONOMETHYL)-DL-PHENYLALANINE, 2 ANALOGS OF O-PHOSPHOTYROSINE [J].

BAYLELACOSTE, M ;

MOULINES, J ;

COLLIGNON, N ;

BOUMEKOUEZ, A ;

DETINGUYMOREAUD, E ;

NEUZIL, E .

TETRAHEDRON, 1990, 46 (23) :7793-7802

[2] DIRECTED LITHIATION OF AROMATIC TERTIARY AMIDES - AN EVOLVING SYNTHETIC METHODOLOGY FOR POLYSUBSTITUTED AROMATICS [J].

BEAK, P ;

SNIECKUS, V .

ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (10) :306-312

[3] A REMARKABLE ACCELERATING EFFECT OF IODIDE-IONS IN THE PHOTOSTIMULATED PHOSPHONYLATION OF BROMOAROMATIC COMPOUNDS [J].

BOUMEKOUEZ, A ;

ABOUTJAUDET, E ;

COLLIGNON, N ;

SAVIGNAC, P .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 440 (03) :297-301

[4] HOMOGENEOUS METALATION OF ALKYLBENZENES [J].

BROADDUS, CD .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (01) :10-&

[5] METALATION OF TOLUENE . QUESTION OF KINETIC VS THERMODYNAMIC CONTROL [J].

BROADDUS, CD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (18) :4174-&

[6]

Creger P. L., 1970, J AM CHEM SOC, V92, P1396, DOI DOI 10.1021/JA00708A048

[7]

Gschwend H.W., 1979, ORG REACT, V26, P1

[8] THE METALATION OF SOME ALKYL ANISOLES [J].

LETSINGER, RL ;

SCHNIZER, AW .

JOURNAL OF ORGANIC CHEMISTRY, 1951, 16 (06) :869-873

[9] COMPARISON OF SYNTHETIC UTILITY OF N-BUTYLLITHIUM AND LITHIUM DIISOPROPYLAMIDE IN METALATIONS OF N,N-DIALKYLTOLUAMIDES [J].

LUDT, RE ;

GRIFFITH.JS ;

MCGRATH, KN ;

HAUSER, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (09) :1668-1674

[10] EFFECT OF TETRAMETHYLETHYLENEDIAMINE ON METALATION OF ORTHO-N,N-DIMETHYLTOLUIDINES AND PARA-N,N-DIMETHYLTOLUIDINES WITH NORMAL-BUTYLLITHIUM - DEUTERATION AND ELECTROPHILIC CONDENSATION OF INTERMEDIATE LITHIOAMINES [J].

LUDT, RE ;

CROWTHER, GP ;

HAUSER, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (05) :1288-&

← 1 2 →