Reaction of o-Quinones in Cyclohexane Solutions with Alkyl Radicals Generated by Solution γ-Irradiation

The structures of products formed in reactions of tert-butylated o-quinones with alkyl radicals were determined by 1H and 13C NMR and two-dimensional 1H-1H NOESY spectroscopy, and also by gas chromatography-mass spectrometry. The major products formed upon γ-irradiation of deaerated solutions of 4-t...

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Bibliographic Details
Published in:Russian journal of general chemistry 2005-09, Vol.75 (9), p.1437-1444
Main Authors: Maslovskaya, L. A., Savchenko, A. I.
Format: Article
Language:English
Subjects:
Alkylation
Benzoquinone
Crystal structure
Crystals
Cyclohexane
Ethers
Gamma irradiation
Gas chromatography
Mass spectrometry
Molecular structure
NMR
Nuclear magnetic resonance
Quinones
Single crystals
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Summary:The structures of products formed in reactions of tert-butylated o-quinones with alkyl radicals were determined by 1H and 13C NMR and two-dimensional 1H-1H NOESY spectroscopy, and also by gas chromatography-mass spectrometry. The major products formed upon γ-irradiation of deaerated solutions of 4-tert-butyl-1,2-benzoquinone and 3,5-di-tert-butyl-1,2-benzoquinone in cyclohexane are monoalkyl ethers and products of addition to the C=C bond. In the case of 4-tert-butyl-1,2-benzoquinone, these are products of mixed O-C and C-C alkylation; the adduct formed by addition of the cyclohexyl radical to the C=C bond in 3,5-di-tert-butyl-1,2-benzoquinone gives an unsymmetrical dimer whose structure was proved by single-crystal X-ray diffraction.
ISSN:1070-3632
1608-3350
DOI:10.1007/s11176-005-0442-4