Catalysis with inorganic cations. VIII. Macrocyclic-yliden malonates: Synthesis, spectroscopic investigation, and metal perchlorate catalysis of the Diels-Alder reaction.

被引：11

作者：

Desimoni, G ^{[1
]}

Faita, G ^{[1
]}

Ricci, M ^{[1
]}

Righetti, PP ^{[1
]}

机构：

[1] Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy

来源：

TETRAHEDRON | 1998年 / 54卷 / 33期

关键词：

D O I：

10.1016/S0040-4020(98)00517-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Macrocyclic-yliden malonates 8-10 have been prepared by Knoevenagel condensation of differently sized crown malonates 5-7 with several aldehydes. The spectroscopic investigations of derivatives 8-10a in several solvents (acetone, acetonitrile, end dichloromethane) in the presence of sodium, lithium, barium, and magnesium perchlorate, evidenced, in some cases, the formation of different complexes, whose structure depends on the cation and on the dimension of the crown-ether unit. The Mg(II) complexation of 9-10 involves both carbonyl oxygen atoms, and this specific interaction has a strong catalytic effect on the Diels-Alder reaction between 9-10b with cyclopentadiene. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9581 / 9602

页数：22

共 18 条

[1] MACROCYCLIC POLYETHER-DIESTER COMPOUNDS AS PHASE-TRANSFER CATALYSTS
ANCHISI, C
CORDA, L
FADDA, AM
MACCIONI, AM
PODDA, G
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (03) : 735 - 737
[2] NEW CLASS OF MACROCYCLIC ETHER-ESTER LIGANDS
BRADSHAW, JS
HANSEN, LD
NIELSEN, SF
THOMPSON, MD
REEDER, RA
IZATT, RM
CHRISTENSEN, JJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (21) : 874 - 875
[3] PREPARATION OF MACROCYCLIC ETHER-ESTERS, THIOETHER-ESTERS, AND ETHER-THIOLESTERS
BRADSHAW, JS
BISHOP, CT
NIELSEN, SF
ASAY, RE
MASIHDAS, DRK
FLANDERS, ED
HANSEN, LD
IZATT, RM
CHRISTENSEN, JJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (23): : 2505 - 2508
[4] Crown ethers: The search for selective ion ligating agents
Bradshaw, JS
Izatt, RM
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (08) : 338 - 345
[5] CATALYSIS WITH INORGANIC CATIONS .2. THE EFFECT OF SOME PERCHLORATES ON DIELS-ALDER REACTION-RATES
CASASCHI, A
DESIMONI, G
FAITA, G
INVERNIZZI, AG
LANATI, S
RIGHETTI, PP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) : 8002 - 8007
[6] SOLVENT EFFECT AS THE RESULT OF FRONTIER MOLECULAR-ORBITAL INTERACTION .4. A PARALLEL BETWEEN SOLVENT EFFECT AND ACID CATALYSIS IN THE INTRAMOLECULAR HETERO-DIELS-ALDER REACTION
CODA, AC
DESIMONI, G
FAITA, G
RIGHETTI, P
TACCONI, G
[J]. TETRAHEDRON, 1989, 45 (03) : 775 - 788
[7] SOLVENT AND SALT EFFECT IN PERICYCLIC-REACTIONS .10. INTRAMOLECULAR ENE REACTIONS VS COMPETITIVE PERICYCLIC PROCESSES - THE EFFECT OF SOLVENTS AND SALTS ON THE REACTION OF 5-BROMO-2-(3-METHYL-2-BUTENYLOXY)BENZYLIDENE-MALONIC ACID DIMETHYL ESTER
DESIMONI, G
FAITA, G
RIGHETTI, PP
VIETTI, F
[J]. HETEROCYCLES, 1995, 40 (02) : 817 - 830
[8] Can a chiral catalyst containing the same ligand/metal components promote the formation of both enantiomers enantioselectively? The bis(oxazoline)-magnesium perchlorate-catalyzed asymmetric Diels-Alder reaction
Desimoni, G
Faita, G
Invernizzi, AG
Righetti, P
[J]. TETRAHEDRON, 1997, 53 (22) : 7671 - 7688
[9] LITHIUM PERCHLORATE CATALYSIS OF THE HETERO-DIELS-ALDER REACTION - A SPECIFIC LITHIUM CATION EFFECT
DESIMONI, G
FAITA, G
RIGHETTI, PP
TACCONI, G
[J]. TETRAHEDRON, 1991, 47 (39) : 8399 - 8406
[10] CATALYSIS WITH INORGANIC CATIONS .3. THE EFFECT OF PERCHLORATES ON THE COMPETITION BETWEEN INTRAMOLECULAR HETERO-DIELS-ALDER AND ENE REACTIONS
DESIMONI, G
FAITA, G
RIGHETTI, PP
[J]. TETRAHEDRON LETTERS, 1995, 36 (16) : 2855 - 2858

← 1 2 →