On the oxidation of dibenzo[fg,ij]pentaphene and dinaphtho[2,1,8,7-defg:2',1',8',7'-ijkl]pentaphene dianions
The dianion of dibenzo[fg,ij]pentaphene has recently been synthesized and shown to react with oxygen, forming the 15,16-dioxo derivative in nearly quantitative yield. Oxidation of the dianion of dinaphtho[2,1,8,7-defg:2',1',8',7'-ijkl]pentaphene under similar conditions...
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| Format: | Article |
| Language: | English |
| Published: |
Serbian Chemical Society
1999-01-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.doiserbia.nb.rs/img/doi/0352-5139/1999/0352-51399910563G.pdf |
| Summary: | The dianion of dibenzo[fg,ij]pentaphene has recently been synthesized and
shown to react with oxygen, forming the 15,16-dioxo derivative in nearly
quantitative yield. Oxidation of the dianion of
dinaphtho[2,1,8,7-defg:2',1',8',7'-ijkl]pentaphene under similar conditions
does not result in any dioxo product. It is shown that these findings are a
consequence of the different modes of cyclic conjugation in the two
dianions. Cyclic conjugation in the mentioned two dianions, as well as in a
number of other structurally related benzenoid dianions is assessed by means
of a quantum-chemical method, developed earlier by the author. |
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| ISSN: | 0352-5139 1820-7421 |