A study on the oxidation of 2-hydroxyporphyrins to porphyrin-α-diones

被引：23

作者：

Beavington, R ^{[1
]}

Rees, PA ^{[1
]}

Burn, PL ^{[1
]}

机构：

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

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 17期

关键词：

D O I：

10.1039/a803633k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Porphyrin-alpha-diones have been used for the preparation of extended rigidly oriented porphyrin systems. Copper 2, free-base 3, and zinc 4 2-hydroxyporphyrins have been prepared by an improved method and treated with a range of oxidants to form the corresponding porphyrin-alpha-diones, 5, 6, and 7 in yields of up to 94%, We have found that the free-base 2-hydroxyporphyrin 3 was easily oxidised and usually gave the best yields of porphyrin-alpha-dione. In this study the most effective general oxidant was determined to be the Dess-Martin periodinane which oxidised all three 2-hydroxyporphyrins to their respective porphyrin-alpha-diones in good yields.

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收藏

页码：2847 / 2851

页数：5

相关论文

共 20 条

[1] SYNTHESIS AND 3RD-ORDER NONLINEAR-OPTICAL PROPERTIES OF A CONJUGATED PORPHYRIN POLYMER [J].

ANDERSON, HL ;

MARTIN, SJ ;

BRADLEY, DDC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (06) :655-657

[2] SYNTHESIS OF TOTALLY RIGID COVALENTLY-LINKED BIS-PORPHYRIN SYSTEMS FOR STUDYING LONG-RANGE ELECTRON-TRANSFER AND ENERGY-TRANSFER PROCESSES [J].

ATKINSON, EJ ;

OLIVER, AM ;

PADDONROW, MN .

TETRAHEDRON LETTERS, 1993, 34 (38) :6147-6150

[3]

BURN PL, 1989, THESIS SYDNEY U AUST

[4] ALDEHYDE-APPENDED TETRAPHENYLPORPHYRIN - A NEW BUILDING-BLOCK FOR PORPHYRIN ARRAYS [J].

BURRELL, AK ;

OFFICER, DL ;

REID, DCW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (08) :900-902

[5] A NEW AND HIGHLY EFFICIENT SYNTHESIS OF HYDROXYPORPHYRINS [J].

CROSSLEY, MJ ;

KING, LG ;

PYKE, SM .

TETRAHEDRON, 1987, 43 (20) :4569-4577

[6] PORPHYRINS WITH APPENDED PHENANTHROLINE UNITS - A MEANS BY WHICH PORPHYRIN PI-SYSTEMS CAN BE CONNECTED TO AN EXTERNAL REDOX CENTER [J].

CROSSLEY, MJ ;

BURN, PL ;

LANGFORD, SJ ;

PRASHAR, JK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (18) :1921-1923

[7] RIGID, LATERALLY-BRIDGED BIS-PORPHYRIN SYSTEMS [J].

CROSSLEY, MJ ;

BURN, PL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (01) :39-40

[8] AN APPROACH TO PORPHYRIN-BASED MOLECULAR WIRES - SYNTHESIS OF A BIS(PORPHYRIN)TETRAONE AND ITS CONVERSION TO A LINEARLY CONJUGATED TETRAKISPORPHYRIN SYSTEM [J].

CROSSLEY, MJ ;

BURN, PL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (21) :1569-1571

[9] A NEW METHOD FOR THE SYNTHESIS OF PORPHYRIN-ALPHA-DIONES THAT IS APPLICABLE TO THE SYNTHESIS OF TRANS-ANNULAR EXTENDED PORPHYRIN SYSTEMS [J].

CROSSLEY, MJ ;

BURN, PL ;

LANGFORD, SJ ;

PYKE, SM ;

STARK, AG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (21) :1567-1568

[10] TAUTOMERISM IN 2-HYDROXY-5,10,15,20-TETRAPHENYLPORPHYRIN - AN EQUILIBRIUM BETWEEN ENOL, KETO, AND AROMATIC HYDROXYL TAUTOMERS [J].

CROSSLEY, MJ ;

HARDING, MM ;

STERNHELL, S .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) :1132-1137