ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .62. 1ST CARBENE COMPLEXES (M = CR, W) WITH CARBOHYDRATE SUBSTITUENTS

被引：42

作者：

AUMANN, R

机构：

[1] Organisch-Chemisches Institut, Universität Münster, Münster, W-4400

来源：

CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 12期

关键词：

CARBENE COMPLEXES OF CARBOHYDRATE DERIVATIVES; VINYLCARBENE CHROMIUM AND TUNGSTEN COMPLEXES; DELTA-D-MANNOFURANOSIDES, 2,3-5,6-DI-O-ISOPROPYLIDENEFURANOSIDES, OF CARBENE COMPLEXES; ALPHA-D-ALLOFURANOSIDES, 1,2-5,6-DI-O-ISOPROPYLIDENEFURRANOSIDES, OF CARBENE COMPLEXES; ALPHA-D-GLUCOFURANOSIDES, 1,2-5,6-DI-O-ISOPROPYLIDENESFURANOSIDES, OF CARBENE COMPLEXES; 1,2-PROPADIENYLIDEN TUNGSTEN COMPLEX;

D O I：

10.1002/cber.19921251224

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first examples of transition metal carbene complexes of carbohydrate derivatives are described: 1,2:5,6-Di-0-isopropyliden-alpha-D-glucofuranose (2a), 1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose (2b), and 2,3:5,6-di-0-isopropyliden-alpha-D-mannofuranose (2c) add regiospecifically at C-3 of alkynylcarbene complexes L(n) = C(OEt) - C = CPh 1 [L(n)M = Cr(CO)5 (a), W(CO)5 (b)] to give vinylcarbene complexes L(n)M = C(OEt) - CH = C(Ph) - O(sugar) (E/Z)-3a-g in good to excellent yields. As a minor side reaction the alkynyl carbene complex (CO)5W = C(OEt) - C = CPh (1 b) isomerises to give the 1,2-propadienylidene complex (CO)5W = C = C = C(OEt)C6H5 (4 b).

引用

页码：2773 / 2778

页数：6

共 11 条

[1] ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .61 PYRIDINES AND PYRIDINIUM SALTS FROM (BETA-AMINOVINYL)CARBENE COMPLEXES (M = CR, W) AND ALKYNES VIA 4(1H)-PYRIDINYLIDENE COMPLEXES
AUMANN, R
HINTERDING, P
[J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (12): : 2765 - 2772
[2] ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .44. CONDENSATION OF METHYL CARBENE COMPLEXES WITH ACID-AMIDES BETA-ALKOXYALKENYL CARBENE AND BETA-AMINOALKENYL CARBENE COMPLEXES OF CHROMIUM AND TUNGSTEN - COMPETITION OF CONDENSATION AND INSERTION
AUMANN, R
HINTERDING, P
[J]. CHEMISCHE BERICHTE-RECUEIL, 1990, 123 (03): : 611 - 620
[3] AUMANN R, UNPUB
[4] CONJUGATE ADDITION OF ALCOHOLS TO ALKYNYLALKOXYCARBENE METAL (CR, W) COMPLEXES
CAMPS, F
LLEBARIA, A
MORETO, JM
RICART, S
VINAS, JM
ROS, J
YANEZ, R
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 401 (1-2) : C17 - C19
[5] ENE VERSUS [2 + 2] CYCLOADDITION REACTIONS OF FISCHER CARBENE COMPLEXES - AN UNUSUAL EFFECT OF SILICON ON THE PRODUCT PARTITION AND THE STEREOSPECIFICITY
FARON, KL
WULFF, WD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) : 6419 - 6420
[6] Fischer E. O., 1976, ANGEW CHEM, V88, P683
[7] Fischer E.O., 1979, INORG SYN, V19, P164
[8] TRANSITION-METAL CARBENE COMPLEXES .43. PHENYL ACETYLENYLETHOXYCARBENE AS LIGAND ON CHROMIUM(O) AND TUNGSTEN(O) PENTACARBONYL STRUCTURE
FISCHER, EO
KREISSL, FR
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1972, 35 (01) : C47 - &
[9] TRANSITION METAL-CARBENE COMPLEX .100. AMINOLYSIS OF CARBENE-ALKOXY GROUP AND ADDITION TO TRIPLE BOND AS COMPETITIVE REACTION - REACTION OF PHENYLACETYLENYL(ETHOXY)CARBENEPENTACARBONYLCHROMIUM AND PHENYLACETYLENYL(ETHOXY)CARBENEPENTACARBONYLTUNGSTEN WITH DIMETHYLAMINE
FISCHER, EO
KALDER, HJ
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 131 (01) : 57 - 64
[10] FISCHER EO, 1976, ANGEW CHEM INT EDIT, V15, P700

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