A Facile Oxidation and Oxygen Insertion of the Cyclopentadiene Ring by Molecular Oxygen in Solution

Oxidation of substituted cyclopentadienes by molecular oxygen afforded the corresponding pyrylium cations in acidic solution, whereby an oxygen atom was inserted into the cyclopentadiene ring. This novel one-step reaction proceeds in a different yield depending on substitution patterns of the cyclop...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-07, Vol.70 (14), p.5768-5770
Main Authors: Gong, Wei-Tao, Ning, Gui-Ling, Li, Xin-Cheng, Wang, Li, Lin, Yuan
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Summary:Oxidation of substituted cyclopentadienes by molecular oxygen afforded the corresponding pyrylium cations in acidic solution, whereby an oxygen atom was inserted into the cyclopentadiene ring. This novel one-step reaction proceeds in a different yield depending on substitution patterns of the cyclopentadiene. A possible reaction pathway and formation mechanism of the pyrylium cation are proposed and discussed.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050715q