Unexpected formation of 3,3a,4,7a-tetrahydrobenzofuran-2,5-diones as well as arene carboxylic acids upon formal double exo nucleophilic addition of R1R2C-COO- to anisolechromium tricarbonyl complexes

被引：21

作者：

Bellassoued, M ^{[1
]}

Chelain, E

Collot, J

Rudler, H

Vaissermann, J

机构：

[1] Univ Gergy Pontoise, CNRS, Lab Synth Organomet, F-95031 Cergy Pontoise, France

[2] Univ Pierre & Marie Curie T 44 45, Lab Synth Organ & Organomet, F-75252 Paris 5, France

[3] Univ Pierre & Marie Curie T 44 45, Chim Met Transit Lab, F-75252 Paris 5, France

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 02期

关键词：

D O I：

10.1039/a808072k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bis(trimethylsily)ketene acetals of the general structure 2 (R-1 = H, Me, R-2 = Me, Et, Pr-i, CMe = CH2) react at -78 degrees C in the presence of (BuOK)-O-t with a series of arenechromium tricarbonyl complexes 3 to give as expected, after oxidation with It followed by silica gel chromatography, arylcarboxylic acids 7. In the case of anisolechromium tricarbonyl 8, besides the m-methoxyarylcarboxylic acids, tetrahydrobenzofuran-2,5-diones 11, are formed as the result of a double nucleophilic addition.

引用

页码：187 / 188

页数：2

共 14 条

[1]

AINSWORTH C, 1972, J ORGANOMET CHEM, V46, P73, DOI 10.1016/S0022-328X(00)90476-5

[2]

[Anonymous], 1990, COMPREHENSIVE ORGANI

[3] REINVESTIGATION OF THE REACTION OF LITHIUM TRIMETHYLSILYL ACETATE ENOLATE WITH CHLOROTRIMETHYLSILANE [J].

BELLASSOUED, M ;

GAUDEMAR, M .

TETRAHEDRON LETTERS, 1990, 31 (02) :209-212

[4] REACTION OF AMINOCARBENE COMPLEXES OF CHROMIUM WITH ALKYNES .3. NEW INSIGHTS INTO THE MECHANISM OF FORMATION AND REARRANGEMENT OF NITROGEN YLIDES [J].

BOUANCHEAU, C ;

PARLIER, A ;

RUDLER, M ;

RUDLER, H ;

VAISSERMANN, J ;

DARAN, JC .

ORGANOMETALLICS, 1994, 13 (12) :4708-4719

[5] HIGHLY REGIOSELECTIVE AROMATIC-SUBSTITUTION ON A DIARYLOXIDETRICARBONYLCHROMIUM COMPLEX [J].

BOUTONNET, JC ;

ROSEMUNCH, F ;

ROSE, E .

TETRAHEDRON LETTERS, 1985, 26 (33) :3989-3992

[6]

CARD RJ, 1973, TETRAHEDRON LETT, P3823

[7] RECENT ADVANCES IN ARENE TRANSFORMATION REACTIONS VIA CHROMIUM COMPLEXES [J].

KUNDIG, EP .

PURE AND APPLIED CHEMISTRY, 1985, 57 (12) :1855-1864

[8] THE TRANSFORMATION OF ARENES INTO ACETYL DIENES VIA NUCLEOPHILIC-ADDITION TO ARENE-CR(CO)3 COMPLEXES AND TRAPPING WITH MEL [J].

KUNDIG, EP ;

SIMMONS, DP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (22) :1320-1322

[9] Asymmetric conversion of arenechromium complexes to functionalized cyclohexenones: Progress toward defining an optimum chiral auxiliary [J].

Pearson, AJ ;

Gontcharov, AV .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (01) :152-162

[10] Controlling the course of nucleophilic additions to ortho-substituted (eta(6)-anisole)tricarbonyl-chromium complexes: Dienol ether formation versus tele-substitution [J].

Schmalz, HG ;

Schellhaas, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (18) :2146-2148

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