Transformations of cyclohexa-1,4-diene under the action of biphenyl—alkali metal systems in THF. Synergistic acceleration by mixtures of lithium and sodium

Journal Article · Thu Mar 15 04:00:00 EDT 2018 · Russian Chemical Bulletin

DOI:https://doi.org/10.1007/S11172-018-2090-Y· OSTI ID:22863364

Yunusov, S. M. ^[1]; Rummel, S. ^[2]; Kalyuzhnaya, E. S.

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1. Russian Academy of Sciences, A. N. Nesmeyanov Institute of Organoelement Compounds (Russian Federation)
2. Leibniz Institute of Surface Modification (Germany)

In the interaction of cyclohexa-1,4-diene (1,4-CHD) with a mixture of biphenyl and metallic lithium or sodium in THF at 20 °C, three processes occur, viz., disproportionation of 1,4-CHD to form benzene and cyclohexene, dehydrogenation of 1,4-CHD to form benzene and molecular hydrogen, and dehydrogenation of 1,4-CHD to form benzene and lithium or sodium hydride. In the case of lithium on the use of an equimolar amount of biphenyl, the isomerization of 1,4-CHD to cyclohexa-1,3-diene is also observed. When the molar ratio Li(Na): Ph{sub 2} increases from 1 : 1 to 2 : 1, i.e., when the reaction is carried out in the presence of an alkali metal solid phase, the overall conversion of 1,4-CHD into benzene and cyclohexene increases. The use of mixtures of lithium and sodium leads to acceleration of the processes of the formation of benzene and cyclohexene. The possible mechanism of the synergistic effect found is discussed.

• OSTI ID: 22863364
• Journal Information: Russian Chemical Bulletin, Journal Name: Russian Chemical Bulletin Journal Issue: 3 Vol. 67; ISSN RCBUEY; ISSN 1066-5285
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
BENZENE
BIPHENYL
DEHYDROGENATION
DIENES
HYDROGEN
ISOMERIZATION
LITHIUM
OXIDATION
REDUCTION
SODIUM
SODIUM HYDRIDES
TETRAHYDROFURAN