Theoretical justification of structure-reactivity correlation of 1,2-benzisoxazole 2-oxides

13C and I5N chemical shift assignments of a number of 1,tbenzisoxazole %oxides and their deoxygenated analogues are reported and discussed. Similarly, assignments for some of the precursors to the N-oxides, ohydroxyaryl ketoximes, are reported. In the N-oxides the 'push-pull' effect of the N -0 dipole is largely localized on the isoxazole unit. A large (cu 39 ppm) upfield shift of the C-3 resonance is caused by the exocyclic oxygen whereas C-7a and, to a lesser extent, C-6 are the most heavily deshielded nuclei. The substituents do not have a significant effect on the C-3 resonance, whereas their effect on the carbocyclic carbons is more pronounced, the most markedly affected being the C-4 and C-6 nuclei. N-Oxidation of 1,2-benzisoxazole causes a large (50.5 ppm) shielding of the "N nucleus.

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Arene-fused 1,2-oxazole N-oxides and derivatives. The impact of the N–O dipole and substitution on their aromatic character and reactivity profile. Can it be a useful structure in synthesis? A theoretical insight

Kozielewicz

Tzeli

Tsoungas

et al. 2014

Struct Chem

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Theoretical justification of structure-reactivity correlation of 1,2-benzisoxazole 2-oxides

Cited by 6 publications

References 12 publications

1,2‐Benzisoxazoles

1,2‐Benzisoxazoles

¹³C and ¹⁵N NMR studies of 1,2‐benzisoxazole 2‐oxides, 1,2‐benzisoxazoles and 2‐hydroxyaryl ketoximes

Arene-fused 1,2-oxazole N-oxides and derivatives. The impact of the N–O dipole and substitution on their aromatic character and reactivity profile. Can it be a useful structure in synthesis? A theoretical insight

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Theoretical justification of structure-reactivity correlation of 1,2-benzisoxazole 2-oxides

Cited by 6 publications

References 12 publications

1,2‐Benzisoxazoles

1,2‐Benzisoxazoles

13C and 15N NMR studies of 1,2‐benzisoxazole 2‐oxides, 1,2‐benzisoxazoles and 2‐hydroxyaryl ketoximes

Arene-fused 1,2-oxazole N-oxides and derivatives. The impact of the N–O dipole and substitution on their aromatic character and reactivity profile. Can it be a useful structure in synthesis? A theoretical insight

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Resources

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¹³C and ¹⁵N NMR studies of 1,2‐benzisoxazole 2‐oxides, 1,2‐benzisoxazoles and 2‐hydroxyaryl ketoximes