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Oxidation and photochemical reactions of 3‐phenyl‐2 H ‐1,4‐benzoxazines
Author(s) -
Battistoni P.,
Bruni P.,
Fava G.,
Tosi G.
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200235
Subject(s) - chemistry , radical , photodissociation , photochemistry , nitroxide mediated radical polymerization , irradiation , reaction mechanism , medicinal chemistry , polymer chemistry , organic chemistry , polymerization , catalysis , radical polymerization , polymer , physics , nuclear physics
3‐Phenyl‐2 H ‐1, 4‐benzoxazines 4‐oxides are light sensitive compounds, irradiation leads to 3‐phenyl‐2 H ‐1,4‐benoxazines and to their 3‐oxidized derivatives, whenever possible. Intermediate oxaziridines are formed during the photolysis and transformed into stable nitroxide radicals. The structure of these radicals was confirmed through peracid oxidation of 3‐phenyl‐2 H ‐1,4‐benzoxazines and 3‐phenyl‐3, 4‐dihydro‐2 H ‐1,4‐benzoxazines. A reaction mechanism is proposed on the basis of experimental observations.