The reactions of nitrogen dioxide with dienes
Abstract
The reaction of nitrogen dioxide with conjugated dienes (2,5-dimethylhexa-2,4-diene, hexa-2,4-diene and 2,3-dimethylbuta-1,3-diene) in organic solvents (mainly hexane, benzene and diethyl ether) results mainly in 1,4-addition giving, with the first two substrates, a mixture of 1,4-dinitro compounds and 1,4-nitro alcohols. The latter are presumably formed from hydrolysis of the intermediate nitronitrites. With 2,3-dimethylbuta-1,3-diene, only the cis and trans 1,4-dinitro compounds were isolated. The reactions effectively stop after the addition of two nitrogen dioxide radicals, only traces of tetrasubstituted products being obtained. With the unconjugated hepta-1,6-diene, addition can be made to occur to both double bonds but, when two equivalents of nitrogen dioxide are added very slowly, the main products derive from addition to one double bond and cyclisation to form cis and trans 1,2-bis(nitromethyl)cyclopentane. All the above reactions give a very complex mixture of products and the product composition depends markedly on the reaction conditions; however, with the conjugated dienes, the 1,4-dinitro compounds can be obtained in yields of ca. 50%. The crystal structure of trans-1,4-dinitro-2,3-dimethylbut-2-ene was determined.
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·NO2-induced nitration is several orders of magnitude greater for the conjugated diene system of cLA compared to the bis-allylic diene system found in linoleic and oleic acids due to resonance stabilization of the radical product formed during ·NO2 radical addition.
“·NO2-induced nitration is also several orders of magnitude greater for the conjugated diene system of cLA compared to the bis-allylic diene system found in linoleic and oleic acids due to resonance stabilization of the radical product formed during ·NO2 radical addition [25].”
From Nitrite and nitrate-dependent generation of anti-inflammatory fatty acid nitroalkenes (2015) · cites this paper as [25]
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- Authors
- Claridge, R. P., Deeming, A. J., Paul, N., Tocher, D. A., & Ridd, J. H.
- ORCID
- Tocher, Derek A.
- Venue
- Journal of the Chemical Society Perkin Transactions 1
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 1998
- Issue
- 21
- Pages
- 3523-3528
- ISSN
- 1364-5463 (ISSN-L)
- 0300-922X
- OpenAlex
- W2101362637
- Cited by
- 15
- References
- 6
- Citations by year
- 2024: 1 · 2018: 1 · 2017: 1 · 2015: 2 · 2013: 1 · 2012: 3
- FWCI
- 0.61
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the Chemical Society Perkin Transactions 1 (publishedVersion)
- UCL Discovery (University College London) (submittedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Cycloaddition Reactions
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Physical Sciences › Chemistry › Spectroscopy › Organic and Inorganic Chemical Reactions
- Keywords
- nitrogen dioxide, conjugated dienes, conjugate addition, 2,3-dimethylbuta-1,3-diene, crystal structure, reaction conditions
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