Generation of Methylene by the Liquid Phase Oxidation of Isobutene with Nitrous Oxide Full article
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Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416 |
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| Output data | Year: 2018, Volume: 74, Number: 27, Pages: 3589-3595 Pages count : 7 DOI: 10.1016/j.tet.2018.05.022 | ||
| Tags | Olefins; Nitrous oxide; 1,3-Dipolar cycloaddition; Oxidation; Methylene | ||
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| Affiliations |
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Funding (1)
| 1 | Federal Agency for Scientific Organizations | 0303-2016-0006 (V.44.1.6) |
Abstract:
The application of nitrous oxide as an alternative oxidant provides new opportunities for selective oxidation of olefins. Here, we studied for the first time the thermal oxidation of isobutene with N2O in the liquid phase. The study revealed that the oxidation proceeds via 1,3-dipolar cycloaddition of N2O to the Cdouble bond; length as m-dashC bond by two routes forming unstable 4,5-dihydro-[1,2,3]-oxadiazole intermediates. The main route (the contribution of 91%) includes the addition of the N2O oxygen to the second carbon atom in olefin. In this case, the oxadiazole decomposes with the Csingle bondC bond cleavage yielding acetone, methylene (:CH2), and N2. The methylene then readily reacts with isobutene and benzene (solvent). The minor route involves the addition of the N2O oxygen to the first carbon atom and the oxadiazole decomposition with a hydrogen shift leading to isobutanal and N2.
The main distinctive feature of the studied reaction is the formation of methylene in high yield.
Cite:
Semikolenov S.
, Ivanov D.
, Babushkin D.
, Malykhin S.
, Kharitonov A.
, Dubkov K.
Generation of Methylene by the Liquid Phase Oxidation of Isobutene with Nitrous Oxide
Tetrahedron. 2018. V.74. N27. P.3589-3595. DOI: 10.1016/j.tet.2018.05.022 WOS Scopus РИНЦ ANCAN OpenAlex
Generation of Methylene by the Liquid Phase Oxidation of Isobutene with Nitrous Oxide
Tetrahedron. 2018. V.74. N27. P.3589-3595. DOI: 10.1016/j.tet.2018.05.022 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
| Submitted: | Jan 17, 2018 |
| Accepted: | May 7, 2018 |
| Published online: | May 17, 2018 |
| Published print: | Jul 5, 2018 |
Identifiers:
| Web of science: | WOS:000436218100014 |
| Scopus: | 2-s2.0-85047076754 |
| Elibrary: | 41780973 |
| Chemical Abstracts: | 2018:986077 |
| Chemical Abstracts (print): | 169:51037 |
| OpenAlex: | W2803870733 |