Novel alkylation, lactonisation and cascade coupling processes mediated by lead tetracarboxylates: the importance of ligands

被引：21

作者：

Moloney, MG ^{[1
]}

Nettleton, E ^{[1
]}

Smithies, K ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Dept Chem, Oxford OX1 3QY, England

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(01)02288-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of lead(IV) tetracarboxylates with carboxylic acids containing unsaturated side chains is reported. At elevated temperature in toluene, facile decarboxylation or lactonisation processes are observed, depending on the length of the carboxylate side chain and in some cases further cascade coupling processes with added nucleophiles are possible. The efficiency of these processes depends on the structure of the carboxylate ligand and the mechanistic implications of these results are briefly discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：907 / 909

页数：3

共 22 条

[1] Alder K, 1936, LIEBIGS ANN CHEM, V524, P189
[2] Copper-mediated cross-coupling of organostannanes with organic iodides at or below room temperature
Allred, GD
Liebeskind, LS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) : 2748 - 2749
[3] OXIDATION OF ALKYL RADICALS FROM DECARBOXYLATION OF ACIDS BY LEAD(4) AND COPPER(2)
BACHA, JD
KOCHI, JK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) : 83 - &
[4] OBSERVATION OF INTERMOLECULAR LIGAND-EXCHANGE IN LEAD(IV) CARBOXYLATES BY 1-D AND 2-D PB-207 NMR-SPECTROSCOPY
BUSTON, JEH
CLARIDGE, TDW
MOLONEY, MG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (04): : 639 - 641
[5] Buston JEH, 1998, MAIN GROUP MET CHEM, V21, P51
[6] BUSTON JEH, 1994, J CHEM RES M, P1101
[7] BIS-LACTONIZATION OF UNSATURATED DIACIDS USING LEAD-TETRAACETATE
COREY, EJ
GROSS, AW
[J]. TETRAHEDRON LETTERS, 1980, 21 (19) : 1819 - 1822
[8] EINE NEUARTIGE SYNTHESE VON BICYCLO[2.2.0]HEXEN-(2)-DERIVATEN
CRIEGEE, R
KRISTINS.H
SEEBACH, D
ZANKER, F
[J]. CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (07): : 2331 - &
[9] Criegee R., 1965, OXIDATION ORGANIC CH, VA
[10] The United Kingdom Chemical Database Service
Fletcher, DA
McMeeking, RF
Parkin, D
[J]. JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 1996, 36 (04): : 746 - 749

← 1 2 3 →