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Bilitrienones from the chemical oxidation of dodecasubstituted porphyrins
- Source :
-
Tetrahedron . Jan2010, Vol. 66 Issue 1, p63-67. 5p. - Publication Year :
- 2010
-
Abstract
- Abstract: 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. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 66
- Issue :
- 1
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 45638944
- Full Text :
- https://doi.org/10.1016/j.tet.2009.10.098