Premium
THERMAL AND PHOTOSENSITIZED DECOMPOSITION OF DIMERIC VALEROPHENONE PEROXIDE FORMED BY OZONATION OF VALEROPHENONE OXIME ETHER *
Author(s) -
Ito Yoshikatsu,
Konishi Mitsuo,
Matsuura Teruo
Publication year - 1979
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1979.tb07114.x
Subject(s) - chemistry , peroxide , photochemistry , biphenyl , thermal decomposition , perylene , ether , oxime , decomposition , photodissociation , yield (engineering) , acetophenone , benzene , medicinal chemistry , organic chemistry , molecule , catalysis , materials science , metallurgy
— Ozonation of valerophenone oxime o‐methyl ether (4) produced a stereoisomeric mixture of crystalline dimeric valerophenone peroxides, 5a and 5b . N‐ n ‐butyl‐N‐methoxybenzamide (6) and N‐methoxy‐N‐phenylvaleramide (7) along with valerophenone (1). Thermolysis of the higher melting peroxide 5a at 170–180°C, where a chemiluminescence was visible from added perylene. gave 1 and butyl benzoate (8) in addition to small amounts of the Norrish Type 11 products of 1. i.e. acetophenone (2) and cis‐ and trans‐ 2‐methyl‐1‐phenylcyclobutanols. Biacetyl‐sensitized photolysis of 5a in benzene yielded 2 in much higher yield in addition to 1, 8, and biphenyl. These results suggest that the triplet excited state of 1 is formed by the decomposition of 1 in low yield in thermolysis and in much higher yield in sensitized photolysis. although some of the Type II products may not arise from the triplet valerophenone.