Electronic Resource
Ruthenium tetroxide oxidation of N-methyl-isoxazolidine: Computational mechanistic study
| العنوان: | Ruthenium tetroxide oxidation of N-methyl-isoxazolidine: Computational mechanistic study |
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| المؤلفون: | Chiacchio, M, Iannazzo, D, Giofrè, S, Romeo, R, Legnani, L, Chiacchio, M. A., Iannazzo, D., Giofrè, S. V., Romeo, R., Legnani, L. |
| بيانات النشر: | Elsevier BV country:NL 2022 |
| نوع الوثيقة: | Electronic Resource |
| مستخلص: | In this paper, we report a mechanistic study of RuO4-catalyzed oxidation on the 2-methylisoxazolidine through computational methods. The investigation was performed taken into consideration that the oxidation could take place on different sites of the substrate. This reaction occurs in two steps, involving a double H-transfer. In particular, the rate-determining one implies a [3 + 2] one-step, but asynchronous mechanism. In the first step, when methyl propanoate is used as solvent, the formation of an ion pair, which affords to the product, is involved. Furthermore, the study highlights that all carbon atoms of the isoxazolidine system, near to the heteroatoms, can undergo the oxidation process. The detected selectivity is correlated to the stability of the corresponding carbocations, leading to the N-methylisoxazolidin-3-one as preferred product. |
| مصطلحات الفهرس: | DFT calculation, Dipolar cycloaddition, Oxazolidinone, Oxidation, Selectivity, Transition metal, info:eu-repo/semantics/article |
| URL: | info:eu-repo/semantics/altIdentifier/wos/WOS:000863178100002 volume:15 issue:9 (September 2022) journal:ARABIAN JOURNAL OF CHEMISTRY |
| الاتاحة: | Open access content. Open access content info:eu-repo/semantics/openAccess |
| ملاحظة: | STAMPA English |
| Other Numbers: | ITBAO oai:boa.unimib.it:10281/391654 10.1016/j.arabjc.2022.104063 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85133353548 1346403249 |
| المصدر المساهم: | BICOCCA OPEN ARCH From OAIster®, provided by the OCLC Cooperative. |
| رقم الانضمام: | edsoai.on1346403249 |
| قاعدة البيانات: | OAIster |
| الوصف غير متاح. |