Abstract
The radical cations of 1-butyl-trans-2,3-diphenyl aziridine (1), 1-butyl-2-phenyl aziridine (2), 1,2-diphenyl aziridine (3) and 1-(p-methoxyphenyl)-2-phenyl aziridine (4) were generated upon laser flash photolysis in aqueous and aqueous acetonitrile solutions by direct photoionisation as indicated by the broad absorption band of the solvated electron above 550 nm as well.
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Notes and references
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Using trans-stilbene as starting material epoxidation with MCPBA formed the corresponding trans-stilbene oxide in yields of 84%. Following the procedure of J. A. Deyrup, C. L. Moyer, J. Org. Chem. 1969 34 175–179., 1-butyl-trans-2,3-diphenyl aziridine 1 was formed with a yield of 58% (ref. 5). The cyclization, as described by.
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Starting with commercially available styrol oxide, the corresponding β-amino alcohol was prepared according to the procedure of N. B. Chapman, D. J. Triggle, J. Chem. Soc. 1963 1385–1400.. The formation of 1-butyl-2-phenyl aziridine 2 occurred as described above (ref. 5).
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For the photolysis a 20 ns pulsed laser LAMBDA Physics EMG 103MSC (λ = 193 and 248 nm) was used at intensities of 20-100 mJ per pulse. Argon- or oxygen-saturated solutions were allowed to flow through a quartz cell (4 mm path length) that was irradiated with laser light in a right-angle geometry with respect to the analyzing light. At least for the aziridine 1 the photoionization is monophotonic due to linear dependence of radical cation yield on laser intensity-see ref. 10, page 58.
The azomethine ylide is protonated by water leading to the iminium cation. Consequently the lifetime of the azomethine ylide decreases with increasing water concentration, see ref. 11.
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Gaebert, C., Siegner, C., Mattay, J. et al. Formation of radical cations of aziridines generated by laser flash photolysis. Photochem Photobiol Sci 3, 990–991 (2004). https://doi.org/10.1039/b410464a
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DOI: https://doi.org/10.1039/b410464a