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Issue 11, 2007
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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.

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

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Article information


Submitted
15 Mar 2007
Accepted
20 Jun 2007
First published
11 Jul 2007

Photochem. Photobiol. Sci., 2007,6, 1170-1176
Article type
Paper

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

L. M. T. Frija, I. D. Reva, A. Gómez-Zavaglia, M. L. S. Cristiano and R. Fausto, Photochem. Photobiol. Sci., 2007, 6, 1170
DOI: 10.1039/B703961A

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