Facile oxidation of a carbaporphyrin at the internal carbon atom: synthesis of novel benzo[18]annulene ketals

被引：58

作者：

Hayes, MJ ^{[1
]}

Spence, JD ^{[1
]}

Lash, TD ^{[1
]}

机构：

[1] Illinois State Univ, Dept Chem, Normal, IL 61790 USA

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 21期

关键词：

D O I：

10.1039/a806394j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of benzocarbaporphyrin 2 with refluxing FeCl3 in CHCl3-alcohol mixtures leads to a remarkably selective oxidation at the interior carbon atom to produce dialkoxy products 5; these species show potentially valuable long wavelength absorptions in their UV-VIS spectra.

引用

收藏

页码：2409 / 2410

页数：2

相关论文

共 10 条

[1]

AYUB J, 1997, CHEM REV, V97, P2267

[2] Carbaporphyrins [J].

Berlin, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (16) :1820-1822

[3] PHOTOSENSITIZERS OF THE PORPHYRIN AND PHTHALOCYANINE SERIES FOR PHOTODYNAMIC THERAPY [J].

BONNETT, R .

CHEMICAL SOCIETY REVIEWS, 1995, 24 (01) :19-33

[4] NEAR-INFRARED ABSORBING DYES [J].

FABIAN, J ;

NAKAZUMI, H ;

MATSUOKA, M .

CHEMICAL REVIEWS, 1992, 92 (06) :1197-1226

[5] Porphyrin synthesis by the ''3+1'' approach: New applications for an old methodology [J].

Lash, TD .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (10) :1197-1200

[6] OXYBENZIPORPHYRIN, A FULLY AROMATIC SEMIQUINONE PORPHYRIN ANALOG WITH PATHWAYS FOR 18-PI-ELECTRON DELOCALIZATION [J].

LASH, TD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (22) :2533-2535

[7] Conjugated macrocycles related to the porphyrins .7. Tropiporphyrin: Tropylium versus porphyrinoid aromaticity [J].

Lash, TD ;

Chaney, ST .

TETRAHEDRON LETTERS, 1996, 37 (49) :8825-8828

[8] Carbaporphyrins [J].

Lash, TD ;

Hayes, MJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (08) :840-842

[9]

MEISSNER UE, 1977, TETRAHEDRON LETT, V18, P3

[10] Novel porphyrinoid macrocycles and their metal complexes [J].

Vogel, E .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (05) :1461-1487