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UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone

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Abstract

The photochemistry and molecular structure of 1-phenyl-4-allyl-tetrazolone (PAT) was studied by FT-IR matrix isolation spectroscopy and DFT(B3LYP)/6-311++G(d,p) calculations. The spectrum of matrix-isolated PAT monomers agrees well with the sum spectrum of three conformers predicted theoretically. UV irradiation (λ > 235 nm) of matrix-isolated PAT induces three types of photofragmentation: (1) production of phenylazide and allyl-isocyanate, with phenylazide then losing N2 to yield 1-aza-1,2,4,6-cycloheptatetraene; (2) formation of phenyl-isocyanate and allylazide; (3) N2 elimination leading to formation of 1-allyl-2-phenyldiaziridin-3-one; this compound partially reacts further to form 1-allyl-1H-benzoimidazol-2(3H)-one. The observed photochemistry of the matrix-isolated PAT is distinct from the preferred photochemical fragmentation in solution, where 3,4-dihydro-3-phenylpyrimidin-2(1H)-one is produced as the primary photoproduct.

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, F.C.T., and CCMAR, University of Algarve, Campus de Gambelas, 8005-039, Faro, Portugal

    L. M. T. Frija & M. L. S. Cristiano

  2. Department of Chemistry, University of Coimbra, Coimbra, P-3004-535, Portugal

    L. M. T. Frija, I. D. Reva, A. Gómez-Zavaglia & R. Fausto

  3. Faculty of Pharmacy and Biochemistry, University of Buenos Aires, C.P. 1113, Buenos Aires, Argentina

    A. Gómez-Zavaglia

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  1. L. M. T. Frija
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  2. I. D. Reva
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  3. A. Gómez-Zavaglia
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  4. M. L. S. Cristiano
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  5. R. Fausto
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Correspondence to R. Fausto.

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Frija, L.M.T., Reva, I.D., Gómez-Zavaglia, A. et al. UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone. Photochem Photobiol Sci 6, 1170–1176 (2007). https://doi.org/10.1039/b703961a

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