Bilitrienones from the chemical oxidation of dodecasubstituted porphyrins

被引：11

作者：

Ongayi, Owendi ^{[1
]}

Vicente, M. Graca H. ^{[1
]}

Ghosh, Brahma ^{[1
]}

Fronczek, Frank R. ^{[1
]}

Smith, Kevin M. ^{[1
]}

机构：

[1] Louisiana State Univ, Dept Chem, Baton Rouge, LA 70803 USA

来源：

TETRAHEDRON | 2010年 / 66卷 / 01期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

TETRAPHENYLPORPHYRIN METAL-COMPLEXES; 4 ISOMERIC BILIVERDINS; MESO-TETRAPHENYLPORPHYRIN; BILE PIGMENT; PHOTO-OXYGENATION; PYRROLE PIGMENTS; LINEAR TETRAPYRROLES; BILATRIENES-ABC; RING-CLEAVAGE; IX-SERIES;

D O I：

10.1016/j.tet.2009.10.098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The structure of the ring-opened product from direct oxidation of meso-tetra-arylporphyrins has been controversial for three decades. Herein we show that bilitrienones 2 are obtained from oxidation of metal-free dodecasubstituted porphyrins 1 in the presence of sodium nitrite, trifluoroacetic acid, and air oxygen. The presence of the para-nonyl groups in 1b stabilized the corresponding bilitrienone 2b, which was characterized by X-ray crystallography. in the absence of the para-nonyl groups bilitrienone 2a undergoes a rapid hydration reaction, giving biladienone 3a as the major isolated product. The molecular structures of 2b and 3a, and the photochemical isomerization of 3a are discussed. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：63 / 67

页数：5

共 50 条

[31] OXIDATION REACTIONS CATALYZED BY METALLO(III) PORPHYRINS
BRUICE, TC
BIOCHEMISTRY, 1987, 26 (13) : 4170 - 4170
[32] OXIDATION OF IRON(II) PORPHYRINS BY ORGANIC MOLECULES
WADE, RS
HAVLIN, R
CASTRO, CE
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (26) : 7530 - &
[33] Oxidation states of manganese porphyrins in water solutions
Ramirez-Gutierrez, O
Claret, J
Ribo, JM
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2005, 9 (06) : 436 - 443
[34] Biomimetic oxidation of indole by Mn(III)porphyrins
Linhares, Margarida
Rebelo, Susana L. H.
Simoes, Mario M. Q.
Silva, Artur M. S.
Neves, M. Graca P. M. S.
Cavaleiro, Jose A. S.
Freire, Cristina
APPLIED CATALYSIS A-GENERAL, 2014, 470 : 427 - 433
[35] PERIPHERAL ATTACK IN REDUCTION AND OXIDATION OF IRON PORPHYRINS
CASTRO, CE
DAVIS, HF
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (19) : 5405 - &
[36] OXIDATION REACTIONS CATALYZED BY METALLO(III) PORPHYRINS
BRUICE, TC
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 194 : 78 - BIOL
[37] OXIDATION OF PORPHYRINS - STRUCTURE OF PRODUCTS OF OCTAETHYLPORPHIN OZONIZATION
SHULGA, AM
BITEVA, IM
GURINOVICH, IF
GRUBINA, LA
GURINOVICH, GP
BIOFIZIKA, 1977, 22 (05): : 771 - 776
[38] PORPHYRINS AND THEIR DERIVATIVES .15. SYNTHESIS AND CHEMICAL-TRANSFORMATIONS OF DIMER PORPHYRINS
ISHKOV, YV
GRUSHEVAYA, ZV
ZHILINA, ZI
SHULGA, AM
ZHURNAL ORGANICHESKOI KHIMII, 1993, 29 (05): : 1054 - 1061
[39] OXIDATION OF PORPHYRINS WITH HYDROGEN PEROXIDE IN SULPHURIC ACID
BONNETT, R
OLDFIELD, D
JOHNSON, AW
DOLPHIN, D
STEPHENS.GF
PROCEEDINGS OF THE CHEMICAL SOCIETY OF LONDON, 1964, (NOV): : 371 - &
[40] Structural, NMR, and EPR studies of S=1/2 and S=3 /2 Fe(III)bis(4-cyanopyridine) complexes of dodecasubstituted porphyrins
Yatsunyk, LA
Walker, FA
INORGANIC CHEMISTRY, 2004, 43 (02) : 757 - 777

← 1 2 3 4 5 →