- PII
- S3034541325060016-1
- DOI
- 10.7868/S3034541325060016
- Publication type
- Article
- Status
- Published
- Authors
- Volume/ Edition
- Volume 66 / Issue number 6
- Pages
- 485-494
- Abstract
- The optical properties and kinetics of consumption of cis- and trans-isomers of aromatic nitroso oxides 4-R–CH–CH–CHNOO (R = OH, NHCOCH) were studied using pulse photolysis and UV-Vis spectrophotometry. The cis-isomer ArNOO is irreversibly transformed into a nitrile oxide intermediate, which then either participates in the (3 + 2)-cycloaddition reaction to the solvent - acetonitrile, or undergoes intramolecular ipso-ortho-cyclization. The substituent R has virtually no effect on the spectral and kinetic characteristics of ArNOO, but shifts the competition between two product formation channels towards ipso-ortho-transformation, leading to the formation of tricyclic isoxazole. Using DFT calculations in the M06L/6-311+G(d,p) + IEFPCM approximation, the details of the mechanisms of the studied transformations are discussed.
- Keywords
- импульсный фотолиз ароматические нитрозооксиды реакционная способность орто-циклизация нитрилоксиды DFT-расчет
- Date of publication
- 08.10.2025
- Year of publication
- 2025
- Number of purchasers
- 0
- Views
- 43
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