Helvetica Chimica Acta p. 777 - 788 (1985)
Update date:2022-08-16
Topics:
Hasler, Erich
Gassmann, Ernst
Wirz, Jacob
The biradical 2,2-dimethyl-1,3-perinaphthadiyl (a) was generated from different precursors, the naphthocyclopropane 1 and the azo copound 2, and from each by three different pathways (pyrolysis, direct photolysis, and triplet sensitization, Scheme 1).The combined evidence from flash photolysis, low-temperature spectroscopy, and product analyses provides a detailed mechanistic picture of the formation and decay of this reactive intermediate which is persistent at 77 K in the triplet ground state (3a) and rather long-lived (400 μs) at room temperature.When formed in its lowest singlet state (1a), the biradical is too short-lived to undergo intersystem crossing to 3a or bimolecular reactions.Thus, 3a is formed exclusively from the excited triplet state of the precursor compounds, 31* or 32*.The monomolecular decay of 3a is retarded by the spin barrier; 3a initiates the polymerization of acrylonitrile and is trapped by 3O2.
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