- Abnormal Products from the Exhaustive Ozone Oxidation of Phenanthrene in HCl/Methanol
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Exhaustive ozone treatment of phenanthrene (6) in HCl/methanol afforded unsubstituted (10a) and chloro-substituted 6H-dibenzopyran-6-ones (10b - d) in addition to the expected dimethyl 2,2'-biphenyldicarboxylate (9c).
- Neumeister, Joachim,Griesbaum, Karl
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p. 1640 - 1642
(2007/10/02)
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- Ozonolysis of Symmetrically 1,2-Disubstituted Ethylenes in HCl/Methanol Solutions: Acid Catalyzed Reactions of Primary Cleavage Products
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The ozonolysis of olefins in 1 M anhydrous solutions of hydrogen chloride in methanol at /= 0 deg C was investigated.Upon warm-up of the ozonolysis products, the peroxidic primary fragmentation products were converted into non peroxidic end-products by HCl-catalyzed reactions.Cyclopentene (1a) and cyclohexene (1b), e.g., afforded mixtures of the corresponding α,ω-dialdehydebis(dimethyl acetals) (8), dimethyl α,ω-dicarboxylates (9), and methyl ω-aldehyde dimethyl acetal carboxylates (10).Norbornene (1c) gave a mixture of the correspondingly substituted 1,3-cyclopentane compounds (8c - 10c), phenanthrene (22) gave a mixture of methyl 2'-formyl-2-biphenylcarboxylate (24a), 2,2'-biphenyldicarbaldehyde (24b), and dimethyl 2,2'-biphenyldicarboxylate (24c).A reaction scheme was advanced for the rationalization of the types and the distribution of the products.It was partly substantiated by model reactions.
- Griesbaum, Karl,Neumeister, Joachim
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p. 2697 - 2706
(2007/10/02)
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