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Synthesis of Halomethyl Isoxazoles/Cyclic Nitrones via Cascade Sequence: 1,2-Halogen Radical Shift as a Key Link.
- Source :
-
Organic Letters . 5/18/2018, Vol. 20 Issue 10, p2906-2910. 5p. - Publication Year :
- 2018
-
Abstract
- A novel iminoxyl radical-promoted dichotomous regioselective 5-exo-trig cyclization onto vinylic halogen/1,2-halogen radical shift sequence is developed for the synthesis of halomethyl isoxazoles/cyclic nitrones using β-halo-β,γ- and γ-halo-γ,δ-unsaturated ketoximes as the substrates and PhI(OAc)2/TEMPO as the oxidation system. DFT calculations reveal that a halogen-bridged three-membered ring transition state is involved in the 1,2-Cl-/Br-atom shift, while the 1,2-I atom migration can be taken into account with an elimination/readdition mechanism. The migration ability was indicated to be ranked in the following order: I > Br > Cl. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ISOXAZOLES
*NITRONES
*HALOGENS
*RADICALS (Chemistry)
*CHEMICAL synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 15237060
- Volume :
- 20
- Issue :
- 10
- Database :
- Academic Search Index
- Journal :
- Organic Letters
- Publication Type :
- Academic Journal
- Accession number :
- 129775661
- Full Text :
- https://doi.org/10.1021/acs.orglett.8b00967