HEXAALKYL TERPYRROLE - A NEW BUILDING-BLOCK FOR THE PREPARATION OF EXPANDED PORPHYRINS

被引：181

作者：

SESSLER, JL ^{[1
]}

WEGHORN, SJ ^{[1
]}

HISEADA, Y ^{[1
]}

LYNCH, V ^{[1
]}

机构：

[1] KYUSHU UNIV,FAC ENGN,DEPT CHEM SCI & TECHNOL,FUKUOKA 812,JAPAN

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 1995年 / 1卷 / 01期

关键词：

AMETHYRIN; ORANGARIN; PORPHYRINOIDS; TERPYRROLES;

D O I：

10.1002/chem.19950010110

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new, general synthesis of the first beta-substituted tetra- and hexaalkyl terpyrroles is described. Also described are two new classes of expanded porphyrins derived from the hexaalkyl terpyrrole. The key step in the terpyrrole formation is the copper(II)-mediated oxidative coupling of the LDA-derived enolates of alpha-keto pyrroles. The first new expanded porphyrin reported here, the so-called ''orangarin'', contains five pyrrolic subunits and two bridging carbon atoms, and is formally a 20 phi-electron nonaromatic macrocycle. The second new class of expanded porphyrins, the ''amethyrins'', are 24 pi-electron nonaromatic macrocycles containing six pyrrole units. Both of these new macrocycles, as well as one of the new terpyrrolic precursors have been structurally characterized by single crystal X-ray diffraction analysis.

引用

页码：56 / 67

页数：12

共 72 条

[1] NOVEL ALKYLMETAL HYDROXIDES - THE CRYSTAL AND MOLECULAR-STRUCTURES OF BIS(MU-HYDROXY)-BIS(TRIS(DIMETHYLPHENYLSILYL)METHYLZINC), [(ME2PHSI)3CZNOH)2] AND MU-4-OXOHEXA(MU-HYDROXY)TETRAKIS(TRIS(TRIMETHYLSILYL)METHYLINDIUM), [O((ME3SI)3CLN)4(OH)6] [J].

ALJUAID, SS ;

BUTTRUS, NH ;

EABORN, C ;

HITCHCOCK, PB ;

ROBERTS, ATL ;

SMITH, JD ;

SULLIVAN, AC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (12) :908-909

[2] INTERMEDIATES IN THE PAAL-KNORR SYNTHESIS OF PYRROLES [J].

AMARNATH, V ;

ANTHONY, DC ;

AMARNATH, K ;

VALENTINE, WM ;

WETTERAU, LA ;

GRAHAM, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6924-6931

[3] A PLANAR ZN4P4 RING IN THE 1ST STRUCTURALLY CHARACTERIZED ZINC DIORGANOPHOSPHIDE - [ZN2(BUT2P)2(OH)(MU-OH)]2 [J].

ARIF, AM ;

COWLEY, AH ;

JONES, RA ;

KOSCHMIEDER, SU .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (17) :1319-1320

[4] NONPLANAR PORPHYRINS - X-RAY STRUCTURES OF (2,3,7,8,12,13,17,18-OCTAETHYL-5,10,15,20-TETRAPHENYLPOPHINATO)ZINC(II) AND (2,3,7,8,12,13,17,18-OCTAMETHYL-5,10,15,20-TETRAPHENYLPORPHINATO)ZINC(II) [J].

BARKIGIA, KM ;

BERBER, MD ;

FAJER, J ;

MEDFORTH, CJ ;

RENNER, MW ;

SMITH, KM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (24) :8851-8857

[5] A NEW SYNTHESIS OF PYRROLES FROM NITROALKENES [J].

BARTON, DHR ;

ZARD, SZ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (16) :1098-1100

[6] SAPPHYRINS - NOVEL AROMATIC PENTAPYRROLIC MACROCYCLES [J].

BAUER, VJ ;

CLIVE, DLJ ;

DOLPHIN, D ;

PAINE, JB ;

HARRIS, FL ;

KING, MM ;

LODER, J ;

WANG, SWC ;

WOODWARD, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (21) :6429-6436

[7]

BRINGMANN G, 1982, LIEBIGS ANN CHEM, P1272

[8]

BRODHURST MJ, 1972, J CHEM SOC P1, P2111

[9] MOLECULAR-STRUCTURE OF LEUCINE AMINOPEPTIDASE AT 2.7-A RESOLUTION [J].

BURLEY, SK ;

DAVID, PR ;

TAYLOR, A ;

LIPSCOMB, WN .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (17) :6878-6882

[10] AMINOSILANES IN ORGANIC-SYNTHESIS - PREPARATION OF NEW EXPANDED PORPHYRIN LIGANDS AND BIMETALLIC TRANSITION-METAL COMPLEXES - CRYSTAL-STRUCTURE OF A TETRAPYRROLE MACROCYCLE DIRHODIUM COMPLEX [J].

CARRE, FH ;

CORRIU, RJP ;

BOLIN, G ;

MOREAU, JJE ;

VERNHET, C .

ORGANOMETALLICS, 1993, 12 (07) :2478-2486

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